Cross-Aldol Reaction of Activated Carbonyls with Nitrosocarbonyl Intermediates: Stereoselective Synthesis toward α-Hydroxy-β-amino Esters and Amides.
Mallik, Sumitava; Bhajammanavar, Vinod; Ramakrishna, Isai; Baidya, Mahiuddin; Organic letters 19 (2017) 3843–3846; doi:10.1021/acs.orglett.7b01721

data_1547110
_publ_section_title
;
 Cross-Aldol Reaction of Activated Carbonyls with Nitrosocarbonyl
 Intermediates: Stereoselective Synthesis toward \a-Hydroxy-\b-amino
 Esters and Amides.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3843
_journal_page_last               3846
_journal_paper_doi               10.1021/acs.orglett.7b01721
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C23 H31 N O5'
_chemical_formula_sum            'C23 H31 N O5'
_chemical_formula_weight         401.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.4153(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3276(3)
_cell_length_b                   8.4210(3)
_cell_length_c                   13.1353(4)
_cell_measurement_reflns_used    3062
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.38
_cell_measurement_theta_min      2.40
_cell_volume                     1137.26(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8409
_diffrn_reflns_point_group_measured_fraction_full 0.794
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.557
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 732 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.2324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.480
_reflns_Friedel_fraction_full    0.557
_reflns_Friedel_fraction_max     0.557
_reflns_number_gt                2496
_reflns_number_total             3179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01721_si_003.cif
_cod_data_source_block           41
_cod_database_code               1547110
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              13537
_shelx_hkl_checksum              58021