Enantioselective Synthesis of 3,4-Dihydropyran Derivatives via Organocatalytic Michael Reaction of α,β-Unsaturated Enones
Yangbin Liu; Xiaohua Liu; Min Wang; Peng He; Lili Lin; Xiaoming Feng; Journal of Organic Chemistry 77 (2012) 4136–4142; doi:10.1021/jo3001047

data_4027152
_publ_section_title
;
 Enantioselective Synthesis of 3,4-Dihydropyran Derivatives via
 Organocatalytic Michael Reaction of \a,\b-Unsaturated Enones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4136
_journal_page_last               4142
_journal_paper_doi               10.1021/jo3001047
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H21 Cl O3'
_chemical_formula_sum            'C18 H21 Cl O3'
_chemical_formula_weight         320.80
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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  Olex2 1.1
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_cell_length_c                   14.9465(8)
_cell_measurement_reflns_used    1042
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      29.1880
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -87.00    3.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0486  -77.0000  -60.0000 90

  2 omega   -4.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0174   38.0000 -120.0000 53
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0082197000
_diffrn_orient_matrix_UB_12      -0.0557204000
_diffrn_orient_matrix_UB_13      0.0062612000
_diffrn_orient_matrix_UB_21      -0.0003689000
_diffrn_orient_matrix_UB_22      -0.0074826000
_diffrn_orient_matrix_UB_23      -0.0470540000
_diffrn_orient_matrix_UB_31      0.0748455000
_diffrn_orient_matrix_UB_32      -0.0061396000
_diffrn_orient_matrix_UB_33      0.0004630000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4434
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'Enhance (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(11)
_refine_ls_extinction_coef       0.048(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0315P)^2^+0.1898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                2074
_reflns_number_total             2865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3001047_si_001.cif
_cod_data_source_block           110720_s2_lyb
_cod_original_cell_volume        1765.30(16)
_cod_database_code               4027152
_chemical_oxdiff_formula         C20H20O3Cl1
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32