The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds: selective C-N bond formation and N-O bond cleavage in one-pot for alpha-amination of ketones
Isai Ramakrishna; Gowri Sankar Grandhi; Harekrishna Sahoo; Mahiuddin Baidya; Chem.Commun. 51 (2015) 13976–; doi:10.1039/C5cc05459A

data_7117716
_publ_section_title
;
 The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl
 compounds: selective C-N bond formation and N-O bond cleavage in one-pot
 for alpha-amination of ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              13976
_journal_paper_doi               10.1039/C5cc05459A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2012
_audit_update_record
;
2015-06-22 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5083(8)
_cell_length_b                   13.3657(9)
_cell_length_c                   9.5834(6)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      1.52
_cell_volume                     1474.08(17)
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_collection       'APEXII (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9969
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.524
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_correction_T_min  0.8801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 610 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0541P)^2^+0.0972P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                1741
_reflns_number_total             2467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05459a2.cif
_cod_data_source_block           ram010
_cod_database_code               7117716
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2012-9
_shelx_res_checksum              35523
_shelx_hkl_checksum              42415