Sequential reactions of trimethylsilyldiazomethane with 4-alkenyl ketones and aldehydes catalyzed by Lewis bases.
Liu, Huaqing; O'Connor, Matthew J; Sun, Chunrui; Wink, Donald J.; Lee, Daesung; Organic letters 15 (2013) 2974–2977; doi:10.1021/ol401124t

data_1556168
_publ_section_title
;
 Sequential reactions of trimethylsilyldiazomethane with 4-alkenyl ketones
 and aldehydes catalyzed by Lewis bases.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2974
_journal_page_last               2977
_journal_paper_doi               10.1021/ol401124t
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C21 H30 N2 O Si'
_chemical_formula_weight         354.56
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.014(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4425(8)
_cell_length_b                   13.9418(13)
_cell_length_c                   17.4523(16)
_cell_measurement_reflns_used    124
_cell_measurement_temperature    298(2)
_cell_volume                     2053.9(3)
_computing_cell_refinement       'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXTL Ver. 6.10'
_computing_publication_material  'SHELXTL Ver. 6.10'
_computing_structure_refinement  'SHELXTL Ver. 6.10'
_computing_structure_solution    'SHELXTL Ver. 6.10 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker AXS area detector'
_diffrn_measurement_method       '0.30\% \w scans'
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18803
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9419
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colorless
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0733P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                3422
_reflns_number_total             4835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401124t_si_002.cif
_cod_data_source_block           cdwdl6
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1556168