Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins.
Davies, Stephen G.; Fletcher, Ai M.; Lee, James A.; Roberts, Paul M.; Souleymanou, Myriam Y.; Thomson, James E.; Zammit, Charlotte M.; Organic & biomolecular chemistry 12 (2014) 2702–2728; doi:10.1039/c4ob00274a

data_7153733
_publ_section_title
;
 Diastereoselective Ireland-Claisen rearrangements of substituted allyl
 \b-amino esters: applications in the asymmetric synthesis of
 C(5)-substituted transpentacins.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2702
_journal_page_last               2728
_journal_paper_doi               10.1039/c4ob00274a
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H36 B1 F4 N1 O2'
_chemical_formula_sum            'C27 H36 B F4 N O2'
_chemical_formula_weight         493.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 98.8420(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.93933(11)
_cell_length_b                   14.19427(18)
_cell_length_c                   10.40085(16)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1304.05(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28792
_diffrn_reflns_theta_full        76.274
_diffrn_reflns_theta_max         76.274
_diffrn_reflns_theta_min         4.302
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.9374
_exptl_absorpt_correction_T_min  0.9224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.14
_refine_ls_abs_structure_details 'Flack (1983), 2570 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5377
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.0004040
_refine_ls_shift/su_mean         0.0000347
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.25P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0696
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0695
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                5232
_reflns_number_total             5399
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.47
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0285
_oxford_refine_ls_scale          9.7(2)
_oxford_reflns_number_all        5378
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c4ob00274a2.cif
_cod_data_source_block           86.HBF4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_formula_sum        'C27 H36 B1 F4 N1 O2'
_cod_database_code               7153733
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE N   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 292,X'S) H   ( 291,X'S) H   ( 293,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 342,X'S) H   ( 341,X'S) H   ( 343,X'S) 
RIDE C   (  35,X'S) H   ( 352,X'S) H   ( 353,X'S) H   ( 351,X'S) 
EQUIV PART (1001,OCC) PART (1002, OCC) 
WEIGHT -1 PART (1002,OCC) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
VIB 0, .002 = F(51) TO B(2) 
CONT F(30) TO B(2) 
CONT F(40) TO B(2) 
CONT F(50) TO B(2) 
CONT F(31) TO B(2) 
CONT F(41) TO B(2) 
U(IJ) 0, .01 = F(51) TO B(2) 
CONT F(30) TO B(2) 
CONT F(40) TO B(2) 
CONT F(50) TO B(2) 
CONT F(31) TO B(2) 
CONT F(41) TO B(2) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;