Rh-Catalyzed Formation of Dioxolanes from α-Alkyl Diazoesters: Diastereoselective Cycloadditions of Carbonyl Ylides with Selectivity over β-Hydride Elimination
Andrew DeAngelis; Patricia Panne; Glenn P. A. Yap; Joseph M. Fox; Journal of Organic Chemistry 73 (2008) 1435–1439; doi:10.1021/jo702308f

data_4023282
_publ_section_title
;
 Rh-Catalyzed Formation of Dioxolanes from \a-Alkyl Diazoesters:
 Diastereoselective Cycloadditions of Carbonyl Ylides with Selectivity
 over \b-Hydride Elimination
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1435
_journal_page_last               1439
_journal_paper_doi               10.1021/jo702308f
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C33 H28 O4'
_chemical_formula_weight         488.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.456(6)
_cell_angle_beta                 103.740(5)
_cell_angle_gamma                106.053(6)
_cell_formula_units_Z            4
_cell_length_a                   10.876(4)
_cell_length_b                   11.998(4)
_cell_length_c                   21.376(7)
_cell_measurement_reflns_used    973
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.25
_cell_volume                     2565.1(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       \w
_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  0.0486
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24189
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     690
_refine_ls_number_reflns         9002
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0869
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2700P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2979
_refine_ls_wR_factor_ref         0.3690
_reflns_number_gt                5474
_reflns_number_total             9002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702308f-File007.cif
_cod_data_source_block           joef048
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_database_code               4023282