Gamma-hydroxynitrile alkylations: electrophile-dependent stereoselectivity.
Mycka, Robert J.; Steward, Omar W.; Fleming, Fraser F.; Organic letters 12 (2010) 3030–3033; doi:10.1021/ol101030r

data_1503446
_publ_section_title
;
 Gamma-hydroxynitrile alkylations: electrophile-dependent
 stereoselectivity.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3030
_journal_page_last               3033
_journal_paper_doi               10.1021/ol101030r
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C13 H25 N O2'
_chemical_formula_sum            'C13 H25 N O2'
_chemical_formula_weight         227.34
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.968(5)
_cell_angle_beta                 91.780(5)
_cell_angle_gamma                99.199(3)
_cell_formula_units_Z            4
_cell_length_a                   6.4938(5)
_cell_length_b                   10.5697(8)
_cell_length_c                   20.8128(15)
_cell_measurement_reflns_used    1551
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.053
_cell_measurement_theta_min      2.7115
_cell_volume                     1408.37(18)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'ORTEP-3 for Windows (Faruggia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart ApexII'
_diffrn_measurement_method       '\f and \w 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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6714
_diffrn_reflns_theta_full        17.10
_diffrn_reflns_theta_max         17.10
_diffrn_reflns_theta_min         0.98
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         1665
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         1665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0463P)^2^+0.8207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                1303
_reflns_number_total             1665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101030r_si_001.cif
_cod_data_source_block           iPr-diol
_cod_database_code               1503446