Quinine-Promoted, Enantioselective Boron-Tethered Diels-Alder Reaction by Anomeric Control of Transition-State Conformation.
Scholl, Katie; Dillashaw, John; Timpy, Evan; Lam, Yu-Hong; DeRatt, Lindsey; Benton, Tyler R.; Powell, Jacqueline P.; Houk, K. N.; Morgan, Jeremy B.; The Journal of organic chemistry 83 (2018) 5756–5765; doi:10.1021/acs.joc.8b00938

data_4034803
_publ_section_title
;
 Quinine-Promoted, Enantioselective Boron-Tethered Diels-Alder Reaction by
 Anomeric Control of Transition-State Conformation.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5756
_journal_page_last               5765
_journal_paper_doi               10.1021/acs.joc.8b00938
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-18
_audit_creation_method           'APEX3 v2015.5-2'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   13.5592(3)
_cell_length_b                   13.5592(3)
_cell_length_c                   5.6888(2)
_cell_measurement_reflns_used    4717
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.485
_cell_measurement_theta_min      3.764
_cell_volume                     905.77(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4928
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.480
_diffrn_reflns_theta_min         3.764
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1142 before and 0.0268 after correction. The Ratio of minimum to maximum transmission is 0.8820. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       needle
_exptl_crystal_F_000             354
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of ethyl acetate and heptane by vapor diffusion'
_exptl_crystal_size_max          1.066
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 838 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1967
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.1444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0728
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                1953
_reflns_number_total             1967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00938_si_001.cif
_cod_data_source_block           morgan01
_cod_original_cell_volume        905.77(5)
_cod_database_code               4034803
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.557
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.975 with sigma of 0.02
 O2-H2
 0.975 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(H14) = Uiso(H13) = Uiso(H12) = Uiso(H11) = Uiso(H10)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C1(H1A), C2(H2A), C5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C11(H11), C12(H12), C13(H13), C4(H4), C3(H3)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              36496
_shelx_hkl_checksum              27864
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id morgan01
_olex2_submission_special_instructions 'No special instructions were received'