Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.
Brawn, Ryan A.; Panek, James S.; Organic letters 11 (2009) 4362–4365; doi:10.1021/ol901692n

data_1504138
_publ_section_title
;
 Synthesis of enantioenriched homopropargylic sulfonamides by a three
 component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4362
_journal_page_last               4365
_journal_paper_doi               10.1021/ol901692n
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C27 H27 Br N2 O6 S Si'
_chemical_formula_weight         615.57
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.7-0'
_cell_angle_alpha                90
_cell_angle_beta                 92.464(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3551(14)
_cell_length_b                   21.005(2)
_cell_length_c                   17.9066(16)
_cell_measurement_reflns_used    4542
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.0378
_cell_measurement_theta_min      3.5677
_cell_volume                     5770.1(9)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 11.2040
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19984
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    3.377
_exptl_absorpt_process_details
;
;
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2528
_refine_diff_density_max         3.190
_refine_diff_density_min         -1.653
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.450
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         20114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.450
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0814
_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^)+(0.0945P)^2^+47.8091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2100
_refine_ls_wR_factor_ref         0.3271
_reflns_number_gt                16113
_reflns_number_total             20114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901692n_si_003.cif
_cod_data_source_block           I
_cod_database_code               1504138