Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol.
Hong, Bor-Cherng; Wu, Ming-Fun; Tseng, Hsing-Chang; Liao, Ju-Hsiou; Organic letters 8 (2006) 2217–2220; doi:10.1021/ol060486+

data_1516752
_publ_section_title
;
 Enantioselective organocatalytic formal [3 + 3]-cycloaddition of
 alpha,beta-unsaturated aldehydes and application to the asymmetric
 synthesis of (-)-isopulegol hydrate and (-)-cubebaol.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2217
_journal_page_last               2220
_journal_paper_doi               10.1021/ol060486+
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C8 H12 O2'
_chemical_formula_weight         140.18
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_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                 103.792(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.773(2)
_cell_length_b                   6.401(2)
_cell_length_c                   8.075(3)
_cell_measurement_temperature    298(2)
_cell_volume                     390.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3456
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9866
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0737P)^2^+0.0167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                1583
_reflns_number_total             1746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060486%2Bsi20060226_113516.cif
_cod_data_source_block           mfw410
_cod_original_cell_volume        390.1(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1516752