4-Alkoxycarbonyl- and Aminocarbonyl-Substituted Isoxazoles as Masked Acrylates and Acrylamides in the Asymmetric Synthesis of Δ^2^-Isoxazolines
Connie K. Y. Lee; Anthony J. Herlt; Gregory W. Simpson; Anthony C. Willis; Christopher J. Easton; Journal of Organic Chemistry 71 (2006) 3221–3231; doi:10.1021/jo0602569

data_4021640
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, ACT 0200, Australia
;
_publ_contact_author_email       ' easton@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        ' Christopher J. Easton '
_publ_contact_author_phone       ' 61 2 6125 8201 '
_publ_section_title
;
 4-Alkoxycarbonyl- and Aminocarbonyl-Substituted Isoxazoles
 as Masked Acrylates and Acrylamides in the Asymmetric
 Synthesis of \D^2^-Isoxazolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3221
_journal_page_last               3231
_journal_paper_doi               10.1021/jo0602569
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H27 N O3 '
_chemical_formula_sum            'C25 H27 N O3'
_chemical_formula_weight         389.49
_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             2001-02-12
_audit_creation_method           'by teXsan v1.8'
_audit_update_record
;
2001-02-13 - Report on C25 H27 N O3
             by Anthony C. Willis
             for Connie K. Y. Lee and Christopher J. Easton
2000-02-14 - passes checkcif tests with minor warnings   
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5610(2)
_cell_length_b                   16.2981(4)
_cell_length_c                   17.6110(5)
_cell_measurement_reflns_used    18155
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.546
_cell_volume                     2170.20(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1994)
;
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full .99
_diffrn_measured_fraction_theta_max .99
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.12666
_diffrn_orient_matrix_UB_12      -0.03492
_diffrn_orient_matrix_UB_13      -0.01519
_diffrn_orient_matrix_UB_21      -0.00815
_diffrn_orient_matrix_UB_22      0.00314
_diffrn_orient_matrix_UB_23      0.06073
_diffrn_orient_matrix_UB_31      -0.01451
_diffrn_orient_matrix_UB_32      0.05469
_diffrn_orient_matrix_UB_33      -0.00477
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.06720
_diffrn_reflns_av_sigmaI/netI    0.130
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24227
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)  implemented in maXus (2000)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832.00
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details
;
The absolute structure has been assigned to match the known chirality of the 
compound's precursors.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.955
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     262
_refine_ls_number_reflns         1562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w = 1/[\s^2^(Fo)] 
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0451
_refine_ls_wR_factor_ref         0.0403
_reflns_number_gt                1562
_reflns_number_total             2195
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            jo0602569si20060207_060923.cif
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C25 H27 N O3 '
_cod_database_code               4021640