Dual Stereoselectivity in the Dialkylzinc Reaction Using (-)-β-Pinene Derived Amino Alcohol Chiral Auxiliaries
Caitlin M. Binder; April Bautista; Marek Zaidlewicz; Marek P. Krzemiński; Allen Oliver; Bakthan Singaram; Journal of Organic Chemistry 74 (2009) 2337–2343; doi:10.1021/jo802371z

data_4024393
_publ_contact_author_address
;
Department of Chemistry and Biochemistry,
University of California, Santa Cruz,
1156 High Street,
Santa Cruz, CA 95064
USA
;
_publ_contact_author_email       singaram@chemistry.ucsc.edu
_publ_contact_author_fax         '+1 831 459 2935'
_publ_contact_author_name        'Bakthan Singaram'
_publ_contact_author_phone       '+1 831 459 3479'
_publ_section_title
;
Dual Stereoselectivity in the Dialkylzinc Reaction Using (-)-\b-Pinene
Derived Amino Alcohol Chiral Auxiliaries
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2337
_journal_page_last               2343
_journal_paper_doi               10.1021/jo802371z
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C13 H23 N O'
_chemical_formula_sum            'C13 H23 N O'
_chemical_formula_weight         209.32
_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                 105.7550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6721(7)
_cell_length_b                   6.0987(4)
_cell_length_c                   10.3902(8)
_cell_measurement_reflns_used    6018
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.19
_cell_volume                     589.86(7)
_computing_cell_refinement       'Bruker SAINT V7.34'
_computing_data_collection       'Bruker APEX-II v2.1'
_computing_data_reduction        'Bruker SAINT V7.34'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       \w/2\q-scans
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6002
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sheldrick, 2004'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0651P)^2^+0.0793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                2655
_reflns_number_total             2830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802371z_si_001.cif
_cod_data_source_block           1a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024393