Stereoselective synthesis of Baylis-Hillman-type adducts via allenolates generated by acyl migration.
Gudimalla, Nagaraju; Fröhlich, Roland; Hoppe, Dieter; Organic letters 6 (2004) 4005–4008; doi:10.1021/ol0483908

data_1506993
_publ_section_title
;
 Stereoselective synthesis of Baylis-Hillman-type adducts via allenolates
 generated by acyl migration.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4005
_journal_page_last               4008
_journal_paper_doi               10.1021/ol0483908
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C25 H33 N O4'
_chemical_formula_weight         411.52
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.24(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.880(1)
_cell_length_b                   18.897(1)
_cell_length_c                   14.191(1)
_cell_measurement_temperature    223(2)
_cell_volume                     2343.4(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\w and \f scans'
_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  0.040
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12808
_diffrn_reflns_theta_full        65.05
_diffrn_reflns_theta_max         65.05
_diffrn_reflns_theta_min         4.68
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  0.9402
_exptl_absorpt_correction_T_min  0.8348
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995 & 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0784P)^2^+0.6623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                2776
_reflns_number_total             3808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0483908si20040813_045949.cif
_cod_data_source_block           hop2521
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1506993