Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes
Erin R. Graham; Rik R. Tykwinski; Journal of Organic Chemistry 76 (2011) 6574–6583; doi:10.1021/jo2008719

data_4026508
_publ_contact_author_address
; Friedrich-Alexander-Universitat Erlangen
  Department Chemie und Pharmazie
  Geschaftsstelle
  Egerlandstr. 3
  91058 Erlangen
  Germany
;
_publ_contact_author_email       rik.tykwinski@chemie.uni-erlangen.de
_publ_contact_author_fax         +49(9131)8522540
_publ_contact_author_name        'Dr. Rik R. Tykwinski'
_publ_contact_author_phone       +49(9131)8526865
_publ_section_title
;
 Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal
 Di- and Triynes to Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6574
_journal_page_last               6583
_journal_paper_doi               10.1021/jo2008719
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H16 O2'
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_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           'manual editing of SHELXL template'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.08550(10)
_cell_length_b                   9.6271(3)
_cell_length_c                   25.6576(7)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.26
_cell_volume                     1256.16(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w 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  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0070
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            11130
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       fragment
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0510P)^2^+0.1787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                1683
_reflns_number_total             1721
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo2008719_si_001.cif
_cod_data_source_block           16
_cod_database_code               4026508