Highly diastereoselective preparation of aldol products using new functionalized allylic aluminum reagents.
Shen, Zhi-Liang; Peng, Zhihua; Yang, Chun-Ming; Helberg, Julian; Mayer, Peter; Marek, Ilan; Knochel, Paul; Organic letters 16 (2014) 956–959; doi:10.1021/ol403692k

data_1513478
_publ_section_title
;
 Highly diastereoselective preparation of aldol products using new
 functionalized allylic aluminum reagents.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              956
_journal_page_last               959
_journal_paper_doi               10.1021/ol403692k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C13 H17 Br O3'
_chemical_formula_sum            'C13 H17 Br O3'
_chemical_formula_weight         301.176
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C13H17BrO3_qo009_knochel
_audit_creation_date
;
'Wed Feb 08 07:15:38 2012'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             08-Feb-12
_cell_angle_alpha                90.00
_cell_angle_beta                 90.016(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7491(6)
_cell_length_b                   32.258(2)
_cell_length_c                   10.4006(14)
_cell_measurement_reflns_used    3631
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.3137
_cell_measurement_theta_min      4.2586
_cell_volume                     2599.8(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega -103.00  -40.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  179.0000  -90.0000 63

  2 omega  -26.00   22.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -97.0000 -130.0000 48

  3 omega  -45.00   52.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2306  -38.0000   60.0000 97

  4 omega   35.00   86.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2306  179.0000   60.0000 51

  5 omega   -5.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2306   38.0000 -120.0000 95

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0260006000
_diffrn_orient_matrix_UB_12      -0.0045926000
_diffrn_orient_matrix_UB_13      0.0638249000
_diffrn_orient_matrix_UB_21      0.0248754000
_diffrn_orient_matrix_UB_22      0.0201946000
_diffrn_orient_matrix_UB_23      0.0196697000
_diffrn_orient_matrix_UB_31      -0.0841201000
_diffrn_orient_matrix_UB_32      0.0074163000
_diffrn_orient_matrix_UB_33      -0.0138044000
_diffrn_radiation_collimation    '0.5 mm collimator'
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16086
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.27
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    3.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.5390(2)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0205P)^2^+2.8926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                3920
_reflns_number_total             5285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403692k_si_002.cif
_cod_data_source_block           qo009
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1513478