One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives.
Pujol, Alba; Calow, Adam D. J.; Batsanov, Andrei S.; Whiting, Andrew; Organic & biomolecular chemistry 13 (2015) 5122–5130; doi:10.1039/c4ob02657h

data_7154381
_publ_section_title
;
 One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived
 imines; functionalisation to homoallylic boronate carboxylate ester
 derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5122
_journal_page_last               5130
_journal_paper_doi               10.1039/c4ob02657h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C22 H19 N'
_chemical_formula_sum            'C22 H19 N'
_chemical_formula_weight         297.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc13xm1p
_audit_creation_date             2014-09-24
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;
Olex2 1.2-beta
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-12-19 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
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'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
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'SHELXL 2014/3 multi-CPU version (Sheldrick, 2008)'
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_diffrn_measured_fraction_theta_full 0.993
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_diffrn_measurement_details
;
  1 omega    0.90   27.00   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0936 -100.0000 -120.0000 87

  2 omega  -85.00   36.20   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0936    0.0000 -150.0000 404

  3 omega   -5.00   88.00   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7186   57.0000   90.0000 310

  4 omega   35.00   71.90   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7186  178.0000  -30.0000 123

  5 omega  -54.00   51.00   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7186  -77.0000  -30.0000 350
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
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_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.993
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_diffrn_reflns_limit_k_min       -30
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_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11019
_diffrn_reflns_point_group_measured_fraction_full 0.993
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_diffrn_reflns_theta_max         27.864
_diffrn_reflns_theta_min         1.867
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73809
_exptl_absorpt_correction_type   multi-scan
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
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_exptl_crystal_size_min          0.08
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.5130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                2917
_reflns_number_total             3426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02657h2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7154381--7154385.cif.'
_cod_original_cell_volume        1657.15(12)
_cod_database_code               7154381
_shelxl_version_number           2014-3
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C3(H3), C16(H16), C13(H13), C21(H21), C14(H14), C12(H12),
 C6(H6), C7(H7), C19(H19), C9(H9), C10(H10), C8(H8), C22(H22), C15(H15),
 C18(H18), C20(H20)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'