Investigation on Lewis Acid Mediated Diels-Alder Reactions of 2-Phosphono-2-alkenoates. Application to Total Synthesis of (\±)-α-Alasken-8-one via Reductive Alkylation of Resulting Adduct
Chuan-Cheng Liao; Jia-Liang Zhu; Journal of Organic Chemistry 74 (2009) 7873–7884; doi:10.1021/jo9017292

data_4024928
_publ_section_title
;
Investigation on Lewis Acid Mediated Diels-Alder Reactions of
2-Phosphono-2-alkenoates. Application to Total Synthesis of
(\+-)-\a-Alasken-8-one via Reductive Alkylation of Resulting Adduct
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7873
_journal_page_last               7884
_journal_paper_doi               10.1021/jo9017292
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C20 H31 N2 O5 P S'
_chemical_formula_sum            'C20 H31 N2 O5 P S'
_chemical_formula_weight         442.50
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                108.664(4)
_cell_angle_beta                 96.593(4)
_cell_angle_gamma                100.843(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0450(5)
_cell_length_b                   10.6569(5)
_cell_length_c                   12.6186(4)
_cell_measurement_reflns_used    7549
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.2891
_cell_measurement_theta_min      4.5079
_cell_volume                     1111.59(9)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_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      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CrysAlis CCD, Oxford Diffraction Ltd.'
_diffrn_measurement_method       'CrysAlis CCD, Oxford Diffraction Ltd.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9390
_diffrn_reflns_theta_full        66.51
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_min         4.51
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0471P)^2^+0.7133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                3584
_reflns_number_total             3838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9017292_si_002_2.cif
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constro' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               4024928