Asymmetric Synthesis of α-Methyl-α-Amino Acids via Diastereoselective Alkylation of (1S)-(+)-3-Carene Derived Tricyclic Iminolactone
Ta-Jung Lu; Cheng-Kun Lin; Journal of Organic Chemistry 76 (2011) 1621–1633; doi:10.1021/jo1022537

data_4026104
_publ_section_title
;
 Asymmetric Synthesis of \a-Methyl-\a-Amino Acids via Diastereoselective
 Alkylation of (1S)-(+)-3-Carene Derived Tricyclic Iminolactone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1621
_journal_page_last               1633
_journal_paper_doi               10.1021/jo1022537
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H25 N O2'
_chemical_formula_sum            'C17 H25 N O2'
_chemical_formula_weight         275.38
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_symmetry_cell_setting           orthorhombic
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.06630(10)
_cell_length_b                   10.27430(10)
_cell_length_c                   20.2326(2)
_cell_measurement_reflns_used    4902
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      71.5370
_cell_measurement_theta_min      4.2994
_cell_volume                     1676.79(3)
_computing_cell_refinement
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CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
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_computing_data_collection
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CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
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_computing_data_reduction
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CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
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_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
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_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6166
_diffrn_reflns_theta_full        71.00
_diffrn_reflns_theta_max         71.64
_diffrn_reflns_theta_min         4.83
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90509
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_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) 
(compiled Aug 27 2009,17:19:36) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0854P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2907
_reflns_number_total             3198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1022537_si_005.cif
_cod_data_source_block           meibuten
_cod_database_code               4026104