Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines.
Outin, Johanne; Quellier, Pauline; Bélanger, Guillaume; The Journal of organic chemistry 85 (2020) 4712–4729; doi:10.1021/acs.joc.9b03449

data_4038076
_publ_section_title
;
 Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich
 Cyclizations to Functionalized Benzoindolizidines and
 Benzoquinolizidines.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4712
_journal_page_last               4729
_journal_paper_doi               10.1021/acs.joc.9b03449
_journal_volume                  85
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H23 N1 O3'
_chemical_formula_sum            'C17 H23 N O3'
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_cell_measurement_temperature    173(2)
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_cell_volume                     760.08(3)
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
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_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.981
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_diffrn_measurement_device       '\k-geometry diffractometer'
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_diffrn_orient_matrix_UB_23      0.917858E-2
_diffrn_orient_matrix_UB_31      0.176682
_diffrn_orient_matrix_UB_32      0.415418E-2
_diffrn_orient_matrix_UB_33      0.943212E-2
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
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;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
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_exptl_crystal_description       needle
_exptl_crystal_F_000             312
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_refine_ls_extinction_coef       0.0096(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.1022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2276
_reflns_number_total             2853
_reflns_threshold_expression     >2\s(I)
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_cod_depositor_comments
'Adding full bibliography for 4038072--4038076.cif.'
_cod_database_code               4038076