Oxazaborolidinone-Catalyzed Enantioselective Diels-Alder Reaction of Acyclic α,β-Unsaturated Ketones
Ram Shanker Singh; Shinya Adachi; Fumi Tanaka; Toyonao Yamauchi; Chieko Inui; Toshiro Harada; Journal of Organic Chemistry 73 (2008) 212–218; doi:10.1021/jo702043g

data_4023176
_publ_section_title
;
 Oxazaborolidinone-Catalyzed Enantioselective Diels-Alder Reaction
 of Acyclic \a,\b-Unsaturated Ketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              212
_journal_page_last               218
_journal_paper_doi               10.1021/jo702043g
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C15 H15 Cl O '
_chemical_formula_sum            'C15 H15 Cl O'
_chemical_formula_weight         246.74
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2007-09-14
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.0660(9)
_cell_length_b                   28.263(2)
_cell_length_c                   5.5141(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    198.1
_cell_measurement_theta_max      28.9
_cell_measurement_theta_min      26.7
_cell_volume                     1257.0(2)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR2002
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2412
_diffrn_reflns_theta_full        66.63
_diffrn_reflns_theta_max         66.63
_diffrn_standards_decay_%        1.48
_diffrn_standards_interval_count 0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.515
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.42
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  275 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.007(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.523
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1617
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1587P)^2^+1.0259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1563
_reflns_number_total             1617
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo702043g-File004.cif
_cod_data_source_block           '_22e-202'
_cod_original_formula_sum        'C15 H15 Cl O '
_cod_database_code               4023176