Highly Stereoselective C-C Bond Formation by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor Carbenoids and Chiral Allylic Alcohols
Zhanjie Li; Brendan T. Parr; Huw M. L. Davies; Journal of the American Chemical Society 134 (2012) 10942–10946; doi:10.1021/ja303023n

data_4118182
_publ_section_title
;
 Highly Stereoselective C-C Bond Formation by Rhodium-Catalyzed Tandem
 Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor
 Carbenoids and Chiral Allylic Alcohols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10942
_journal_page_last               10946
_journal_paper_doi               10.1021/ja303023n
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C21 H28 O3'
_chemical_formula_weight         328.43
_chemical_name_systematic
; 
 ? 
;
_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                   5.4496(4)
_cell_length_b                   13.7116(8)
_cell_length_c                   25.4795(15)
_cell_measurement_temperature    173(2)
_cell_volume                     1903.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16001
_diffrn_reflns_theta_full        65.51
_diffrn_reflns_theta_max         65.51
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.592
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             712
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.895
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.895
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0841
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2394
_refine_ls_wR_factor_ref         0.2531
_reflns_number_gt                2678
_reflns_number_total             3218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303023n_si_010.cif
_cod_data_source_block           zl_xii_121
_cod_database_code               4118182