Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.
Spielmann, Kim; Xiang, Ming; Schwartz, Leyah A.; Krische, Michael J.; Journal of the American Chemical Society 141 (2019) 14136–14141; doi:10.1021/jacs.9b08715

data_4128807
_publ_section_title
;
 Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols:
 Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of
 Phthalimido-Allene via Hydrogen Auto-Transfer.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14136
_journal_page_last               14141
_journal_paper_doi               10.1021/jacs.9b08715
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
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_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
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_cell_length_b                   9.5929(2)
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'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'
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'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'
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'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'
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_computing_publication_material  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

SHELXT. Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. 
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Agilent SuperNova with an Atlas S2 CCD'
_diffrn_measurement_method       \w-scans
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_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
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_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.699
_diffrn_reflns_theta_min         4.197
_diffrn_source                   'sealed microfocus tube'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00
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_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5735
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.2440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.868
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                5638
_reflns_number_total             5735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08715_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4128807
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              25146
_shelx_hkl_checksum              84872