A Mechanistic Investigation of the Asymmetric Meerwein-Schmidt-Ponndorf-Verley Reduction Catalyzed by BINOL/AlMe~3~-Structure, Kinetics, and Enantioselectivity
Christopher R. Graves; Hongying Zhou; Charlotte L. Stern; SonBinh T. Nguyen; Journal of Organic Chemistry 72 (2007) 9121–9133; doi:10.1021/jo070563u

data_4022956
_publ_section_title
;
 A Mechanistic Investigation of the Asymmetric
 Meerwein-Schmidt-Ponndorf-Verley Reduction Catalyzed by
 BINOL/AlMe~3~-Structure, Kinetics, and Enantioselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9121
_journal_page_last               9133
_journal_paper_doi               10.1021/jo070563u
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C33 H39 Al O5'
_chemical_formula_weight         542.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.599(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.363(8)
_cell_length_b                   11.064(3)
_cell_length_c                   8.571(2)
_cell_measurement_temperature    153(2)
_cell_volume                     2820.4(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13108
_diffrn_reflns_theta_full        28.86
_diffrn_reflns_theta_max         28.86
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.113
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6461
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                5576
_reflns_number_total             6461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070563u-File001.cif
_cod_data_source_block           s74m1m
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4022956