Patent ID: 11866398
Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY
Field: Organic fine chemistry (Chemistry)
Classification: CPC C  B | IPC B  C

Claim 1:
2. The method according to claim 1, wherein the ruthenium catalyst is a stereoretentive ruthenium olefin metathesis catalyst represented by Formula (I) is, X is O or S;
Y is O or S;
Z is N or CR32;
W is O, halogen, NR33 or S;
R1 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R2 can form a spiro compound or together with R3 or together with R4 can form a polycyclic ring;
R2 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl or together with R1 can form a spiro compound or together with R3 or together with R4 can form a polycyclic ring;
R3 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl or together with R2 or together with R1 can form a polycyclic ring or together with R4 can form a spiro compound;
R4 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R3 can form a spiro compound or together with R2 or together with R1 can form a polycyclic ring;
R5 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R6 can form an optionally substituted polycyclic ring;
R6 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R5 or together with R7 can form an optionally substituted polycyclic ring;
R7 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl optionally substituted C3-8 cycloalkenyl, or together with R6 or together with R8 can form an optionally substituted polycyclic ring;
R8 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R7 or together with R9 can form an optionally substituted polycyclic ring;
R9 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R8 can form an optionally substituted polycyclic ring;
R10 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R11 can form an optionally substituted polycyclic ring;
R11 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl or together with R10 or together with R12 can form an optionally substituted polycyclic ring;
R12 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R11 or together with R13 can form an optionally substituted polycyclic ring;
R13 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R14 or together with R12 can form an optionally substituted polycyclic ring;
R14 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R13 can form a polycyclic ring;
R15 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl, or together with R16 can form an optionally substituted polycyclic ring;
R16 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl, or together with R15 or together with R17 can form an optionally substituted polycyclic ring;
R17 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl, or together with R18 or together with R16 can form an optionally substituted polycyclic ring;
R18 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl, or together with R17 can form an optionally substituted polycyclic ring;
R19 is H, optionally substituted C1-24 alkyl, —C(R34)(R35)COOR36, —C(R34)(R35)C(O)H, —C(R34)(R35)C(O)R37, —C(R34)(R35)CR38(OR39)(OR40), —C(R34)(R35)C(O)NR41R42, —C(R34)(R35)C(O)NR41OR40, —C(O)R25, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R33 can form an optionally substituted heterocyclic ring or is nil when W is halogen;
R20 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl or together with R21 can form a polycyclic ring;
R21 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl or together with R20 or together with R22 can form a polycyclic ring;
R22 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl or together with R21 or together with R23 can form a polycyclic ring;
R23 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl or together with R22 can form a polycyclic ring;
R24 is H, optionally substituted C1-24 alkyl, halogen, —C(O)R25, —OR26, CN, —NR27R28, NO2, —CF3, —S(O)xR29, —P(O)(OH)2, —OP(O)(OH)2, —SR31, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R25 is OH, OR30, NR27R28, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl,
R26 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R27 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R28 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R29 is H, optionally substituted C1-24 alkyl, OR26, —NR27R28, optionally substituted heterocycle, optionally substituted C3-8 cycloalkyl, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R30 is optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R31 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R32 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R33 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl, optionally substituted C3-8 cycloalkenyl, or together with R19 can form an optionally substituted heterocyclic ring;
R34 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R35 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R36 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R37 is optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R38 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R39 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R40 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R41 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl;
R42 is H, optionally substituted C1-24 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl or optionally substituted C3-8 cycloalkenyl; and
x is 1 or 2.