Copper/Lewis base cooperatively catalyzed asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with azomethine ylides.
Hu, Yimin; Yan, Zhengyang; Shi, Wangyu; Liao, Jianning; Liu, Min; Pan, Ting; Wang, Wei; Wu, Yongjun; Hao, Xianghong; Guo, Hongchao; Chemical communications (Cambridge, England) 57 (2021) 8059–8062; doi:10.1039/d1cc02861h

data_7128658
_publ_section_title
;
 Copper/Lewis base cooperatively catalyzed asymmetric allylic alkylation
 of Morita-Baylis-Hillman carbonates with azomethine ylides.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8059
_journal_page_last               8062
_journal_paper_doi               10.1039/d1cc02861h
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H25 N O4'
_chemical_formula_sum            'C23 H25 N O4'
_chemical_formula_weight         379.44
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-08 deposited with the CCDC.	2021-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                82.4130(10)
_cell_angle_beta                 86.4550(10)
_cell_angle_gamma                89.4660(10)
_cell_formula_units_Z            2
_cell_length_a                   5.8434(2)
_cell_length_b                   9.9102(3)
_cell_length_c                   17.9362(5)
_cell_measurement_reflns_used    8478
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      59.20
_cell_measurement_theta_min      2.49
_cell_volume                     1027.61(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9670
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        59.192
_diffrn_reflns_theta_max         59.192
_diffrn_reflns_theta_min         5.427
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0939 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.8852.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 2438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         5509
_refine_ls_number_restraints     405
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.1081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                5357
_reflns_number_total             5509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02861h2.cif
_cod_data_source_block           20210708_0m_a
_cod_depositor_comments          'Adding full bibliography for 7128658.cif.'
_cod_database_code               7128658
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C32(H32), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C10(H10), C16(H16), C15(H15), C19(H19),
 C18(H18), C17(H17), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C42(H42),
  C43(H43), C44(H44), C45(H45), C46(H46)
2.d X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C38(H38A,H38B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              97369
_shelx_hkl_checksum              70366
_olex2_submission_special_instructions 'No special instructions were received'