Asymmetric Synthesis of gem-Difluoromethylenated Dihydroxypyrrolizidines and Indolizidines
Watcharaporn Thaharn; Teerawut Bootwicha; Darunee Soorukram; Chutima Kuhakarn; Samran Prabpai; Palangpon Kongsaeree; Patoomratana Tuchinda; Vichai Reutrakul; Manat Pohmakotr; Journal of Organic Chemistry 77 (2012) 8465–8479; doi:10.1021/jo301327s

data_4027548
_publ_contact_author_address
;Department of Chemistry, Faculty of Science
Mahidol University
Rama VI, Bangkok 10400, Thailand
;
_publ_contact_author_email       palangpon@gmail.com
_publ_contact_author_fax         +662-354-7151
_publ_contact_author_name        ' Palangpon Kongsaeree'
_publ_contact_author_phone       ' +662-201-5190'
_publ_section_title
;
 Asymmetric Synthesis of gem-Difluoromethylenated Dihydroxypyrrolizidines
 and Indolizidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8465
_journal_page_last               8479
_journal_paper_doi               10.1021/jo301327s
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C21 H41 F2 N O4 Si2'
_chemical_formula_sum            'C21 H41 F2 N O4 Si2'
_chemical_formula_weight         465.730
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9430(2)
_cell_length_b                   12.3857(4)
_cell_length_c                   21.2265(7)
_cell_measurement_reflns_used    3987
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     2614.07(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.08223
_diffrn_orient_matrix_UB_12      0.04795
_diffrn_orient_matrix_UB_13      -0.03246
_diffrn_orient_matrix_UB_21      -0.02934
_diffrn_orient_matrix_UB_22      -0.00061
_diffrn_orient_matrix_UB_23      -0.07522
_diffrn_orient_matrix_UB_31      -0.02104
_diffrn_orient_matrix_UB_32      0.04141
_diffrn_orient_matrix_UB_33      0.00787
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17503
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.64
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       Priam
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         7443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0429P)^2^+0.6667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                5888
_reflns_number_total             7443
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301327s_si_001_2.cif
_cod_data_source_block           11-trans
_cod_original_cell_volume        2614.06(13)
_cod_database_code               4027548