Catalytic Enantioselective Intermolecular Hydroacylation: Rhodium-Catalyzed Combination of β-S-Aldehydes and 1,3-Disubstituted Allenes
James D. Osborne; Helen E. Randell-Sly; Gordon S. Currie; Andrew R. Cowley; Michael C. Willis; Journal of the American Chemical Society 130 (2008) 17232–17233; doi:10.1021/ja8069133

data_4108883
_publ_contact_author             'Michael C. Willis'
_publ_contact_author_email       michael.willis@chem.ox.ac.uk
_publ_section_title
;
 Catalytic Enantioselective Intermolecular Hydroacylation:
 Rhodium-Catalyzed Combination of \b-S-Aldehydes and 1,3-Disubstituted
 Allenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17232
_journal_page_last               17233
_journal_paper_doi               10.1021/ja8069133
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H24 O1 S1'
_chemical_formula_sum            'C21 H24 O S'
_chemical_formula_weight         324.49
_chemical_name_systematic
;
 (+)-(S)-(E)-1-(2-(methylthio)phenyl)-2-styrylhexan-1-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-04-30
_audit_creation_method           CRYSTALS_ver_12.51
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0431(2)
_cell_length_b                   9.3052(2)
_cell_length_c                   21.7992(2)
_cell_measurement_reflns_used    62253
_cell_measurement_temperature    150
_cell_measurement_theta_max      30
_cell_measurement_theta_min      5
_cell_volume                     1834.36(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            62253
_diffrn_reflns_theta_full        30.011
_diffrn_reflns_theta_max         30.011
_diffrn_reflns_theta_min         5.100
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.10
_exptl_crystal_thermal_history
; 
The material was crystallised at ambient temperature. A suitable crystal 
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. 
;
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.14
_refine_ls_abs_structure_details 'Flack, 2310 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0792
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.003450
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.470 0.220 0.202 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0387
_refine_ls_wR_factor_gt          0.0348
_refine_ls_wR_factor_ref         0.0348
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                4824
_reflns_number_total             5324
_reflns_threshold_expression     I>3.00u(I)
_oxford_structure_analysis_title 5402
_cod_data_source_file            ja8069133_si_002.cif
_cod_data_source_block           Entry3-Table2
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C21 H24 O1 S1'
_cod_database_code               4108883