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_4024394
_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         'C14 H25 N O'
_chemical_formula_sum            'C14 H25 N O'
_chemical_formula_weight         223.35
_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                   6.1721(6)
_cell_length_b                   10.2840(11)
_cell_length_c                   19.865(2)
_cell_measurement_reflns_used    4291
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.23
_cell_volume                     1260.9(2)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12831
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.05
_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  0.9906
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sheldrick, 2004'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0482P)^2^+0.1090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                2838
_reflns_number_total             3129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802371z_si_002.cif
_cod_data_source_block           1b
_cod_database_code               4024394