Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine.
Comins, Daniel L.; Schilling, Stefan; Zhang, Yanchen; Organic letters 7 (2005) 95–98; doi:10.1021/ol047824w

data_1506491
_publ_section_title
;
 Asymmetric synthesis of 3-substituted isoindolinones: application to the
 total synthesis of (+)-lennoxamine.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              95
_journal_page_last               98
_journal_paper_doi               10.1021/ol047824w
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C25 H29 N O3 '
_chemical_formula_sum            'C25 H29 N O3'
_chemical_formula_weight         391.51
_chemical_name_systematic
;
(3R)-3-Methyl-N-[(((1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexyl)oxy)carbonyl)
-2,3-dihydro-isoindol-1-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.2443(5)
_cell_length_b                   16.1149(7)
_cell_length_c                   15.7912(7)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    148
_cell_measurement_theta_max      18.00
_cell_measurement_theta_min      16.50
_cell_volume                     2097.96(18)
_computing_cell_refinement       'Nonius CAD4 Argus'
_computing_data_collection       'Nonius CAD4 Argus'
_computing_data_reduction        'NRCVAX DATRD2'
_computing_molecular_graphics    NRCVAX
_computing_publication_material  'NRCVAX TABLES Jan 94 Version'
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      148
_diffrn_measurement_device       'Nonius CAD-4    '
_diffrn_measurement_method       'Omega scan b/P/b        '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .013
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4206
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.20
_diffrn_standards_decay_%        2.2
_diffrn_standards_interval_time  80
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .08
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       prism
_exptl_crystal_F_000             840.48
_exptl_crystal_preparation
;
? # Insert crystal growing method here.
;
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .12
_refine_diff_density_max         .18
_refine_diff_density_min         -.14
_refine_ls_abs_structure_details
; The structure of the molecule included a chiral auxillary ((-)TCC) of
known absolute configuration.  The handeness of the known centers were
fixed.
;
_refine_ls_extinction_coef       1.61(15)
_refine_ls_extinction_method     Larson
_refine_ls_goodness_of_fit_ref   1.26
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         3277
_refine_ls_R_factor_all          .031
_refine_ls_R_factor_gt           .031
_refine_ls_shift/su_max          .000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/(\s^2^(F)+ .0003F^2^) '
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .033
_refine_ls_wR_factor_ref         .033
_reflns_number_gt                3277
_reflns_number_total             3660
_reflns_threshold_expression     'Inet > 1.0\s(Inet)'
_cod_data_source_file            ol047824wsi20041028_110753.cif
_cod_data_source_block           (-)TCC
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C25 H29 N O3 '
_cod_database_code               1506491