Metal Carbene-Promoted Sequential Transformations for the Enantioselective Synthesis of Highly Functionalized Cycloheptadienes
Liang Deng; Anthony J. Giessert; Oksana O. Gerlitz; Xing Dai; Steven T. Diver; Huw M. L. Davies; Journal of the American Chemical Society 127 (2005) 1342–1343; doi:10.1021/ja045173t

data_4111423
_publ_section_title
;
 Metal Carbene-Promoted Sequential Transformations for the
 Enantioselective Synthesis of Highly Functionalized Cycloheptadienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1342
_journal_page_last               1343
_journal_paper_doi               10.1021/ja045173t
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C24 H25 Br O5'
_chemical_formula_weight         473.35
_chemical_name_common            BrPh-cyclopropane
_chemical_name_systematic
; 
 (1S, 2S) 2-(Acetoxy-phenyl-methyl)-2-(2-ethoxy-vinyl)-1-(4-bromo-
 phenyl)-cyclopropanecarboxylic acid methyl ester 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.5420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3815(2)
_cell_length_b                   16.4835(6)
_cell_length_c                   10.9674(4)
_cell_measurement_reflns_used    870
_cell_measurement_temperature    90(1)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.30
_cell_volume                     1105.91(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19263
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    1.891
_exptl_absorpt_correction_T_max  0.7980
_exptl_absorpt_correction_T_min  0.4833
_exptl_absorpt_correction_type   'empirical SADABS 2.05'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      0
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    'riding model and ideal CH3 groups'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         6354
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0208P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                6092
_reflns_number_total             6354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja045173tsi20040810_095250.cif
_cod_data_source_block           BrPhcyclopropane
_cod_database_code               4111423