Steric Factors Direct Baylis-Hillman and Aldol Reactions in Titanium Tetrachloride Mediated Coupling between α-Keto Esters and Cyclohex-2-enone Derivatives
Deevi Basavaiah; Bandaru Sreenivasulu; Anumolu Jaganmohan Rao; Journal of Organic Chemistry 68 (2003) 5983–5991; doi:10.1021/jo0342424

data_4022423
_publ_section_title
;
 Steric Factors Direct Baylis-Hillman and Aldol Reactions
 in Titanium Tetrachloride Mediated Coupling between
 \a-Keto Esters and Cyclohex-2-enone Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5983
_journal_page_last               5991
_journal_paper_doi               10.1021/jo0342424
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30
_chemical_name_systematic
'Ethyl syn-2-hydroxy-2-phenyl-2-(cyclohex-5-en-1-on-2-yl)ethanoate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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                 93.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7653(18)
_cell_length_b                   9.2536(19)
_cell_length_c                   17.751(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1437.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1203
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3485
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0605
_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^)+(0.1400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2601
_reflns_number_gt                1458
_reflns_number_total             3287
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0342424si20030227_030336.cif
_cod_data_source_block           for_compound_5
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022423