Reaction of Corey Ylide with α,β-Unsaturated Ketones: Tuning of Chemoselectivity toward Dihydrofuran Synthesis.
Chagarovsky, Alexey O.; Budynina, Ekaterina M.; Ivanova, Olga A.; Villemson, Elena V.; Rybakov, Victor B.; Trushkov, Igor V.; Melnikov, Mikhail Ya; Organic letters 16 (2014) 2830–2833; doi:10.1021/ol500877c

data_1516048
_publ_contact_author             'Dr Victor B. Rybakov'
_publ_section_title
;
 Reaction of Corey Ylide with \a,\b-Unsaturated Ketones: Tuning of
 Chemoselectivity toward Dihydrofuran Synthesis.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2830
_journal_page_last               2833
_journal_paper_doi               10.1021/ol500877c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_chemical_melting_point_gt       374
_chemical_melting_point_lt       375
_chemical_name_systematic
; 
 Ethyl 4-(1-benzyl-1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-carboxylate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.597(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0605(5)
_cell_length_b                   10.1253(7)
_cell_length_c                   19.2983(11)
_cell_measurement_reflns_used    4280
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.85
_cell_volume                     1965.1(2)
_computing_cell_refinement       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_collection       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_reduction        '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_molecular_graphics    '<i>Ortep--3</i> (Farrugia,   1997)'
_computing_publication_material  '<i>WinGX</i>    (Farrugia,   1999)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick,  2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick,  2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'Hybride pixel array detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS Pilatus--100K'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
 99 runs, 1190 frames, detector distance = 80 mm
;
_diffrn_measurement_device       'Four cyrcle diffractometer'
_diffrn_measurement_device_type  'STADI--VARI Pilatus--100K'
_diffrn_measurement_method       'Rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'Plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source         'LFF Sealed Tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15014
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'SEIFERT Iso--Debyeflex 3003'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             768
_exptl_crystal_preparation       'Petroleum ether / ethyl acetate'
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0727
_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^)+(0.1568P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.2695
_reflns_number_gt                1702
_reflns_number_total             3761
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol500877c_si_002.cif
_cod_data_source_block           ch1083
_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/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 

 Adding full bibliography for 1516047--1516048.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1516048