Catalytic Asymmetric Iterative/Domino Aldehyde Cross-Aldol Reactions for the Rapid and Flexible Synthesis of 1,3-Polyols.
Lin, Luqing; Yamamoto, Kumiko; Mitsunuma, Harunobu; Kanzaki, Yamato; Matsunaga, Shigeki; Kanai, Motomu; Journal of the American Chemical Society 137 (2015) 15418–15421; doi:10.1021/jacs.5b11192

data_4129868
_publ_section_title
;
 Catalytic Asymmetric Iterative/Domino Aldehyde Cross-Aldol Reactions for
 the Rapid and Flexible Synthesis of 1,3-Polyols.
;
_journal_issue                   49
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15418
_journal_page_last               15421
_journal_paper_doi               10.1021/jacs.5b11192
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 91.6756(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2912(2)
_cell_length_b                   6.8967(2)
_cell_length_c                   12.5196(3)
_cell_measurement_reflns_used    6274
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.5
_cell_volume                     715.59(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0792
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7499
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0232P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                1935
_reflns_number_total             2402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b11192_si_002.cif
_cod_data_source_block           ydkr
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129868