CuH-Catalyzed Enantioselective Intramolecular Reductive Aldol Reactions Generating Three New Contiguous Asymmetric Stereocenters
Bruce H. Lipshutz; Benjamin Amorelli; John B. Unger; Journal of the American Chemical Society 130 (2008) 14378–14379; doi:10.1021/ja8045475

data_4108581
_publ_section_title
;
 CuH-Catalyzed Enantioselective Intramolecular Reductive Aldol Reactions
 Generating Three New Contiguous Asymmetric Stereocenters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14378
_journal_page_last               14379
_journal_paper_doi               10.1021/ja8045475
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H18 O2'
_chemical_formula_weight         170.24
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.939(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3896(8)
_cell_length_b                   9.8022(15)
_cell_length_c                   9.3448(13)
_cell_measurement_temperature    200(2)
_cell_volume                     493.62(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1734
_diffrn_reflns_av_sigmaI/netI    0.1083
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1199
_diffrn_reflns_theta_full        49.08
_diffrn_reflns_theta_max         49.08
_diffrn_reflns_theta_min         4.73
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.335
_exptl_absorpt_correction_T_min  0.161
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         699
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0804
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1915P)^2^+0.0510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2087
_reflns_number_gt                691
_reflns_number_total             699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8045475_si_002.cif
_cod_data_source_block           Lip
_cod_database_code               4108581