Catalytic Asymmetric Claisen Rearrangement of Unactivated Allyl Vinyl Ethers
Maryll E. Geherty; Robert D. Dura; Scott G. Nelson; Journal of the American Chemical Society 132 (2010) 11875–11877; doi:10.1021/ja1039314

data_4102954
_publ_section_title
;
 Catalytic Asymmetric Claisen Rearrangement of Unactivated Allyl Vinyl
 Ethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11875
_journal_page_last               11877
_journal_paper_doi               10.1021/ja1039314
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H22 Br N O'
_chemical_formula_weight         372.30
_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                   5.0268(12)
_cell_length_b                   15.831(4)
_cell_length_c                   22.862(6)
_cell_measurement_reflns_used    1230
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      17.755
_cell_measurement_theta_min      2.196
_cell_volume                     1819.3(8)
_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      203(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Smart Apex CCD'
_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  0.1035
_diffrn_reflns_av_sigmaI/netI    0.0903
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14271
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    2.264
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_correction_T_min  0.5906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                1938
_reflns_number_total             3185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1039314_si_003.cif
_cod_data_source_block           mgn114s
_cod_original_cell_volume        1819.4(8)
_cod_database_code               4102954