A highly stereo-controlled protocol to prepare pipecolic acids based on Heck and cyclohydrocarbonylation reactions
Arena, Giada; Cini, Elena; Petricci, Elena; Randino, Rosario; Taddei, Maurizio; Organic Chemistry Frontiers 2 (2015) 526–; doi:10.1039/C5QO00025D

data_1553099
_publ_section_title
;
 A highly stereo-controlled protocol to prepare pipecolic acids based on
 Heck and cyclohydrocarbonylation reactions
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              526
_journal_paper_doi               10.1039/C5QO00025D
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H29 N O3'
_chemical_formula_sum            'C25 H29 N O3'
_chemical_formula_weight         391.49
_chemical_name_systematic
;
tert-Butyl (1R,2S,3R,6R,7S,9S)-6-phenyl-8-oxa-2-
azatetracyclo[7.7.0.02,7.011,16]hexadeca-11(16),12,14-
triene-3-carboxylate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-23 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5720(4)
_cell_length_b                   15.4800(10)
_cell_length_c                   25.4858(16)
_cell_measurement_reflns_used    1891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0851
_cell_measurement_theta_min      2.3926
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_computing_cell_refinement
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
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_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            8096
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
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_diffrn_reflns_theta_min         2.632
_exptl_absorpt_coefficient_mu    0.077
_exptl_crystal_density_diffrn    1.183
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_refine_diff_density_min         -0.096
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;
 Flack x determined using 535 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4981
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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^)+(0.0150P)^2^] where P=(Fo^2^+2Fc^2^)/3'
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