Stereocontrol in synthesis of homoallylic amines. Syn selective direct allylation of hydrazones with allylboronic acids.
Das, Arindam; Alam, Rauful; Eriksson, Lars; Szabó, Kálmán J; Organic letters 16 (2014) 3808–3811; doi:10.1021/ol501699x

data_1516967
_publ_contact_author             'Kalman Szabo'
_publ_section_title
;
 Stereocontrol in synthesis of homoallylic amines. Syn selective direct
 allylation of hydrazones with allylboronic acids.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3808
_journal_page_last               3811
_journal_paper_doi               10.1021/ol501699x
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C20 H24 N2 O'
_chemical_formula_sum            'C20 H24 N2 O'
_chemical_formula_weight         308.41
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'Manual editing of the cif file produced by SHELXL-97'
_cell_angle_alpha                102.932(3)
_cell_angle_beta                 112.881(3)
_cell_angle_gamma                94.888(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1480(3)
_cell_length_b                   10.4716(4)
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_cell_measurement_temperature    293(2)
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.5467
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scan at different \f to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
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_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13447
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_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88169
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colour_less
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
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_refine_diff_density_max         0.230
_refine_diff_density_min         -0.117
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_refine_ls_extinction_coef       0.040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3194
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_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.2139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                2811
_reflns_number_total             3194
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol501699x_si_004.cif
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_cod_depositor_comments
'Adding full bibliography for 1516966--1516967.cif.'
_cod_original_cell_volume        903.43(6)
_cod_database_code               1516967