Catalytic, asymmetric hypervinylogous Mukaiyama aldol reactions of extended furan-based silyl enolates.
Curti, Claudio; Battistini, Lucia; Sartori, Andrea; Lodola, Alessio; Mor, Marco; Rassu, Gloria; Pelosi, Giorgio; Zanardi, Franca; Casiraghi, Giovanni; Organic letters 13 (2011) 4738–4741; doi:10.1021/ol2020626

data_1502470
_publ_section_title
;
 Catalytic, asymmetric hypervinylogous Mukaiyama aldol reactions of
 extended furan-based silyl enolates.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4738
_journal_page_last               4741
_journal_paper_doi               10.1021/ol2020626
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_sum            'C28 H37 Br O5'
_chemical_formula_weight         533.49
_chemical_name_systematic
;
(R,Z)-1-(4-bromophenyl)-4,4-dimethyl-3-[(5-oxofuran-
2(5H)-ylidene)]pentyl (1R,2S,5R)-2-isopropyl-5-methyl
cyclohexyl carbonate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.426(2)
_cell_length_b                   18.992(2)
_cell_length_c                   6.2050(4)
_cell_measurement_temperature    293(2)
_cell_volume                     2760.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3021
_diffrn_reflns_theta_full        69.82
_diffrn_reflns_theta_max         69.82
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.91(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0483
_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^)+(0.1052P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                2203
_reflns_number_total             3021
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2020626_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1502470