Asymmetric synthesis of propargylic alcohols via aldol reaction of aldehydes with ynals promoted by prolinol ether–transition metal–Brønsted acid cooperative catalysis
Gómez-Bengoa, Enrique; García, Jesús M.; Jiménez, Sandra; Lapuerta, Irati; Mielgo, Antonia; Odriozola, José M.; Otazo, Itziar; Razkin, Jesús; Urruzuno, Iñaki; Vera, Silvia; Oiarbide, Mikel; Palomo, Claudio; Chemical Science 4 (2013) 3198–; doi:10.1039/c3sc51027a

data_1514759
_publ_section_title
;
 Asymmetric synthesis of propargylic alcohols via aldol reaction of
 aldehydes with ynals promoted by prolinol ether--transition
 metal--Br\/onsted acid cooperative catalysis
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              3198
_journal_paper_doi               10.1039/c3sc51027a
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 I2 O2'
_chemical_formula_sum            'C18 H18 I2 O2'
_chemical_formula_weight         520.12
_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                   7.7537(2)
_cell_length_b                   8.7833(3)
_cell_length_c                   28.0793(10)
_cell_measurement_temperature    100(2)
_cell_volume                     1912.29(11)
_computing_cell_refinement       'SAINT V7.12A (Bruker 2004)'
_computing_data_collection       'Apex2 V.1.0-27(Bruker 2005)'
_computing_data_reduction        'SAINT and XPREP Version 6.14, 2003'
_computing_molecular_graphics    'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_publication_material  'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_structure_refinement  'SHELXL-97 in SHELXTL ver. 6.12, 2001'
_computing_structure_solution    'SHELXS-97 in SHELXTL ver. 6.12, 2001'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20538
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    3.293
_exptl_absorpt_correction_T_max  0.9477
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   Multi-scan?
_exptl_absorpt_process_details
;
SADABS program multi-scan
Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.248
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0204
_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^)+(0.0350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                3225
_reflns_number_total             3395
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51027a.txt
_cod_data_source_block           anc1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1514759