Switch in regioselectivity of epoxide ring-opening by changing the organometallic reagent.
Gálvez, José A; Díaz de Villegas, María D; Badorrey, Ramón; López-Ram-de-Víu, Pilar; Organic & biomolecular chemistry 9 (2011) 8155–8162; doi:10.1039/c1ob06216f

data_7152090
_publ_section_title
;
 Switch in regioselectivity of epoxide ring-opening by changing the
 organometallic reagent.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8155
_journal_page_last               8162
_journal_paper_doi               10.1039/c1ob06216f
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H21 N O'
_chemical_formula_sum            'C14 H21 N O'
_chemical_formula_weight         219.32
_chemical_name_systematic
;
(R)-2-[(R)-1-hydroxy-3-phenylpropyl]piperidine
;
_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                   6.3355(6)
_cell_length_b                   7.4390(8)
_cell_length_c                   26.291(2)
_cell_measurement_reflns_used    4795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8706
_cell_measurement_theta_min      3.1557
_cell_volume                     1239.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.929
_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  0.1681
_diffrn_reflns_av_sigmaI/netI    0.0915
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            21730
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0295P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                1856
_reflns_number_total             2988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06216f.txt
_cod_data_source_block           shelxl
_cod_database_code               7152090