Multistereocenter-Containing Cyclopentanoids from Ynamides via Oxazolidinone-Controlled Nazarov Cyclization.
Manchala, Narasimhulu; Law, Hanson Y. L.; Kerr, Daniel J.; Volpe, Rohan; Lepage, Romain J.; White, Jonathan M.; Krenske, Elizabeth H.; Flynn, Bernard L.; The Journal of organic chemistry 82 (2017) 6511–6527; doi:10.1021/acs.joc.7b00082

data_4037471
_publ_section_title
;
 Multistereocenter-Containing Cyclopentanoids from Ynamides via
 Oxazolidinone-Controlled Nazarov Cyclization.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6511
_journal_page_last               6527
_journal_paper_doi               10.1021/acs.joc.7b00082
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C25 H27 N O3'
_chemical_formula_weight         389.48
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1206(2)
_cell_length_b                   10.1349(2)
_cell_length_c                   21.0311(5)
_cell_measurement_reflns_used    10061
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      74.4869
_cell_measurement_theta_min      4.2008
_cell_volume                     2157.19(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18563
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         4.20
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BRICK
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.4764
_exptl_crystal_size_mid          0.2845
_exptl_crystal_size_min          0.0860
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0508P)^2^+1.2334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                3724
_reflns_number_total             3875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00082_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4037471