Stabilized alpha-helix-catalyzed enantioselective epoxidation of alpha,beta-unsaturated ketones.
Nagano, Masanobu; Doi, Mitsunobu; Kurihara, Masaaki; Suemune, Hiroshi; Tanaka, Masakazu; Organic letters 12 (2010) 3564–3566; doi:10.1021/ol101435w

data_1503121
_publ_section_title
;
 Stabilized alpha-helix-catalyzed enantioselective epoxidation of
 alpha,beta-unsaturated ketones.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3564
_journal_page_last               3566
_journal_paper_doi               10.1021/ol101435w
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C63 H111 N9 O15, 2(H2 O) '
_chemical_formula_sum            'C63 H115 N9 O17'
_chemical_formula_weight         1270.65
_chemical_melting_point          235
_chemical_name_systematic
; 
 Boc-{L-Leu-L-Leu-[(1S,3S)-Ac5c(OM)]}3-OMe
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_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            8
_cell_length_a                   12.247(2)
_cell_length_b                   15.641(3)
_cell_length_c                   77.051(15)
_cell_measurement_reflns_used    9130
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      20.48
_cell_measurement_theta_min      2.11
_cell_volume                     14760(5)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINTPLUS (Bruker, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXD (Seldrick & Gould, 1996)'
_diffrn_ambient_temperature      240(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS SMART APEX (CCD area detector)'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator
'Bruker AXS Montel (conforcal multilayer optics)'
_diffrn_radiation_source         'MacScience M18XCE (rotating anode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       77
_diffrn_reflns_limit_l_min       -77
_diffrn_reflns_number            75027
_diffrn_reflns_theta_full        20.82
_diffrn_reflns_theta_max         20.82
_diffrn_reflns_theta_min         1.06
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_count 75027
_diffrn_standards_interval_time  720
_diffrn_standards_number         192
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.543
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             5536
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel pairs'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     1603
_refine_ls_number_reflns         8620
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0830
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1269P)^2^+18.7208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2190
_refine_ls_wR_factor_ref         0.2274
_reflns_number_gt                7280
_reflns_number_total             8620
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol101435w_si_002.cif
_cod_data_source_block           nano1
_cod_original_cell_volume        14759(5)
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_database_code               1503121