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_4021639
_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 unk
_chemical_formula_moiety         'C15 H17 N O3 '
_chemical_formula_sum            'C15 H17 N O3'
_chemical_formula_weight         259.30
_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             2000-10-16
_audit_creation_method           'by teXsan v1.8'
_audit_update_record
;
2000-10-16 - Report on C15 H17 N O3
             by Anthony C. Willis
             for Connie K. Y. Lee and Christopher J. Easton
2000-10-16 - passes checkcif tests with no warnings   
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8777(2)
_cell_length_b                   9.1491(2)
_cell_length_c                   17.3590(4)
_cell_measurement_reflns_used    16219
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      4.076
_cell_volume                     1409.95(5)
_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       ' omega scans with CCD '
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.11116
_diffrn_orient_matrix_UB_12      0.01101
_diffrn_orient_matrix_UB_13      -0.00729
_diffrn_orient_matrix_UB_21      -0.01409
_diffrn_orient_matrix_UB_22      0.00221
_diffrn_orient_matrix_UB_23      0.05714
_diffrn_orient_matrix_UB_31      0.01155
_diffrn_orient_matrix_UB_32      0.10872
_diffrn_orient_matrix_UB_33      -0.00042
_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  0.07465
_diffrn_reflns_av_sigmaI/netI    0.100
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21431
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         4.20
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)  implemented in maXus (1999)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552.00
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.314
_refine_ls_goodness_of_fit_ref   1.446
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_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         0.0533
_refine_ls_wR_factor_ref         0.0510
_reflns_number_gt                1449
_reflns_number_total             1860
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            jo0602569si20060207_060859.cif
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C15 H17 N O3 '
_cod_database_code               4021639