Enantioselective Synthesis of β-Allenoates via Phosphine Catalysed and ZnI2 Promoted Preparation of Oxozolidines and Propargylamines using Chiral Amines, 1-Alkynes and Propiolates.
Periasamy, Mariappan; Mohan, Lakavathu; Satyanarayana, Iddum; Reddy, Polimera Obula; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02632

data_4033266
_publ_section_title
;
 Enantioselective Synthesis of \b-Allenoates via Phosphine Catalysed and
 ZnI2 Promoted Preparation of Oxozolidines and Propargylamines using
 Chiral Amines, 1-Alkynes and Propiolates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02632
_journal_year                    2017
_chemical_absolute_configuration S
_chemical_formula_moiety         'C22 H25 N O3'
_chemical_formula_sum            'C22 H25 N O3'
_chemical_formula_weight         351.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.474(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1961(6)
_cell_length_b                   6.5619(3)
_cell_length_c                   12.9957(8)
_cell_measurement_reflns_used    5277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.65
_cell_volume                     938.86(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10684
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.445
_diffrn_reflns_theta_min         2.652
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.1781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                3565
_reflns_number_total             3996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02632_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4033266
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              59794
_shelx_hkl_checksum              42350