Ni(ii)-Catalyzed enantioselective Mukaiyama–Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters
Xie, Lei; Ma, Hongli; Li, Jiaqi; Yu, Yuan; Qin, Zhaohai; Fu, Bin; Organic Chemistry Frontiers 4 (2017) 1858–; doi:10.1039/C7QO00370F

data_1553807
_publ_section_title
;
 Ni(ii)-Catalyzed enantioselective Mukaiyama--Mannich reaction between
 silyl enol ethers and cyclic N-sulfonyl \a-ketiminoesters
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1858
_journal_paper_doi               10.1039/C7QO00370F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C21 H23 N O5 S'
_chemical_formula_sum            'C21 H23 N O5 S'
_chemical_formula_weight         401.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
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  Olex2 1.1
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;
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2017-03-04 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
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'A short history of SHELX (Sheldrick, 2007)/Bruker'
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;
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omega____ theta____ kappa____ phi______ frames
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  2 omega   30.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000 -150.0000 26

  3 omega   72.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -32.00   40.00   1.0000    1.5000
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  5 omega   79.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  6 omega    0.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  7 omega   10.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000   90.0000 92

  8 omega   71.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  150.0000 34

  9 omega  -30.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -150.0000 66

 10 omega   28.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000    0.0000 40

 11 omega  100.00  143.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 43

 12 omega   97.00  134.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 37

 13 omega  121.00  178.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 57

 14 omega   56.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 42

 15 omega   40.00   82.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 42

 16 omega   50.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 48

 17 omega   42.00   96.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 54

 18 omega   61.00   96.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
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 19 omega   80.00  106.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -103.0000  -50.0000 26

 20 omega   58.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 40

 21 omega   70.00  157.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
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 22 omega  150.00  176.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 26

 23 omega   72.00  122.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
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 24 omega  113.00  138.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 25

 25 omega   75.00  104.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 29

 26 omega   44.00   83.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 39

 27 omega   38.00  107.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -103.0000   -2.0000 69

 28 omega   83.00  167.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 84

 29 omega   70.00  116.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -114.0000  150.0000 46
;
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_diffrn_orient_matrix_UB_13      0.0240259000
_diffrn_orient_matrix_UB_21      0.1529478000
_diffrn_orient_matrix_UB_22      0.0041036000
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_diffrn_orient_matrix_UB_31      -0.1125456000
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_diffrn_orient_matrix_UB_33      0.0742713000
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_av_R_equivalents  0.0305
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_diffrn_reflns_limit_l_max       16
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_diffrn_reflns_number            6248
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.600
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_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(15)
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0678P)^2^+0.0517P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0986
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_cod_data_source_file            c7qo00370f2.cif
_cod_data_source_block           exp_4772
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_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
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_shelx_hkl_checksum              87942
_shelx_res_checksum              81482
_shelx_shelxl_version_number     2014/7