A two-step, stereoselective synthesis of nine- and ten-membered carbocycles from phthalates.
Prado, Gustavo; Veiga, Alberte X.; Fernández-Nieto, Fernando; Paleo, M. Rita; Sardina, F. Javier; Organic letters 17 (2015) 2054–2057; doi:10.1021/acs.orglett.5b00552

data_1554878
_publ_section_title
;
 A two-step, stereoselective synthesis of nine- and ten-membered
 carbocycles from phthalates.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2054
_journal_page_last               2057
_journal_paper_doi               10.1021/acs.orglett.5b00552
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C29 H36 N2 O4'
_chemical_formula_sum            'C29 H36 N2 O4'
_chemical_formula_weight         476.6
_chemical_name_common            JSGP952CRIS
_chemical_name_systematic
;
 ((1S,5S,6Z,8Z)-cyclonona-6,8-diene-1,5-diyl)bis(methylene) 
bis(((S)-1-phenylethyl)carbamate)
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-14T11:29:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.717(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5270(4)
_cell_length_b                   16.7982(7)
_cell_length_c                   9.3056(4)
_cell_measurement_reflns_used    3660
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.89
_cell_measurement_theta_min      2.43
_cell_measurement_wavelength     0.71073
_cell_volume                     1300.22(10)
_computing_cell_refinement       'APEX2 v2013.4-1 (Bruker AXS, 2013)'
_computing_data_collection       'APEX2 v2013.4-1 (Bruker AXS, 2013)'
_computing_data_reduction        'APEX2 v2013.4-1 (Bruker AXS, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker X8 kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19210
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER AXS - SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.4310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2287
_reflns_number_total             2756
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol5b00552_si_002.cif
_cod_data_source_block           js10gua1n
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554878