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_4108582
_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            'C15 H20 O2'
_chemical_formula_weight         232.31
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.699(2)
_cell_length_b                   14.472(5)
_cell_length_c                   15.647(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1290.5(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3391
_diffrn_reflns_theta_full        46.65
_diffrn_reflns_theta_max         46.65
_diffrn_reflns_theta_min         4.16
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.075
_refine_diff_density_min         -0.084
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.377
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.377
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                1053
_reflns_number_total             1081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8045475_si_003.cif
_cod_data_source_block           lip
_cod_original_cell_volume        1290.6(8)
_cod_database_code               4108582