Organocatalytic Sequential One-Pot Double Cascade Asymmetric Synthesis of Wieland-Miescher Ketone Analogues from a Knoevenagel/Hydrogenation/Robinson Annulation Sequence: Scope and Applications of Organocatalytic Biomimetic Reductions
Dhevalapally B. Ramachary; Mamillapalli Kishor; Journal of Organic Chemistry 72 (2007) 5056–5068; doi:10.1021/jo070277i

data_4023969
_publ_contact_author_address
; 
School of Chemistry
University of Hyderabad
Hyderabad
500046
India
;
_publ_contact_author_email       ramsc@uohyd.ernet.in
_publ_contact_author_fax         +91-40-23012460
_publ_contact_author_name        Dr.D.B.Ramachary
_publ_contact_author_phone       +91-40-23134816
_publ_section_title
;
 Organocatalytic Sequential One-Pot Double Cascade Asymmetric
 Synthesis of Wieland-Miescher Ketone Analogues from a
 Knoevenagel/Hydrogenation/Robinson Annulation Sequence:
 Scope and Applications of Organocatalytic Biomimetic Reductions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5056
_journal_page_last               5068
_journal_paper_doi               10.1021/jo070277i
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         ' C19 H20 O2 '
_chemical_formula_sum            'C19 H20 O2'
_chemical_formula_weight         280.35
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.194(3)
_cell_length_b                   13.671(3)
_cell_length_c                   22.720(6)
_cell_measurement_reflns_used    3520
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.49
_cell_volume                     3166.1(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13389
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0787
_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^)+(0.0349P)^2^+2.4128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1617
_reflns_number_gt                2192
_reflns_number_total             3094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070277isi20070209_033732.cif
_cod_data_source_block           dbr7bb
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4023969