Highly Diastereoselective Preparation of Homoallylic Alcohols Containing Two Contiguous Quaternary Stereocenters in Acyclic Systems from Simple Terminal Alkynes
Bishnu Dutta; Noga Gilboa; Ilan Marek; Journal of the American Chemical Society 132 (2010) 5588–5589; doi:10.1021/ja101371x

data_4102336
_publ_section_title
;
 Highly Diastereoselective Preparation of Homoallylic Alcohols Containing
 Two Contiguous Quaternary Stereocenters in Acyclic Systems from Simple
 Terminal Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5588
_journal_page_last               5589
_journal_paper_doi               10.1021/ja101371x
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C18 H26 O3'
_chemical_formula_weight         290.39
_chemical_name_common            'Marek-51 (Bishu)'
_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                91.26(2)
_cell_angle_beta                 90.96(2)
_cell_angle_gamma                95.55(3)
_cell_formula_units_Z            2
_cell_length_a                   7.242(1)
_cell_length_b                   7.939(2)
_cell_length_c                   14.711(3)
_cell_measurement_reflns_used    6929
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      1.38
_cell_volume                     841.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6929
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                1618
_reflns_number_total             3066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101371x_si_001.cif
_cod_data_source_block           Marek-51
_cod_database_code               4102336