Synthesis of Axially Chiral Amino Acid and Amino Alcohols via Additive-Ligand-Free Pd-Catalyzed Domino Coupling Reaction and Subsequent Transformations of the Product Amidoaza[5]helicene
Takumi Furuta; Junya Yamamoto; Yuki Kitamura; Ayano Hashimoto; Hyuma Masu; Isao Azumaya; Toshiyuki Kan; Takeo Kawabata; Journal of Organic Chemistry 75 (2010) 7010–7013; doi:10.1021/jo101524t

data_4025737
_publ_section_title
;
 Synthesis of Axially Chiral Amino Acid and Amino Alcohols via
 Additive-Ligand-Free Pd-Catalyzed Domino Coupling Reaction and Subsequent
 Transformations of the Product Amidoaza[5]helicene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7010
_journal_page_last               7013
_journal_paper_doi               10.1021/jo101524t
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C38 H33 N O3'
_chemical_formula_weight         551.65
_chemical_name_systematic
' (dl)-tert-Butyl 2'-(hydroxydiphenylmethyl)-1,1'-binaphthyl-2-ylcarbamate'
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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            8
_cell_length_a                   19.2960(10)
_cell_length_b                   11.2886(6)
_cell_length_c                   26.8332(15)
_cell_measurement_reflns_used    5579
_cell_measurement_temperature    120
_cell_measurement_theta_max      23.91
_cell_measurement_theta_min      2.22
_cell_volume                     5844.9(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            27918
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         10827
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                8404
_reflns_number_total             10827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101524t_si_006.cif
_cod_data_source_block           a0908011mas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025737