A tether controlled exo-selective trans-annular Diels-Alder (TADA) reaction.
Felzmann, Wolfgang; Arion, Vladimir B.; Mieusset, Jean-Luc; Mulzer, Johann; Organic letters 8 (2006) 3849–3851; doi:10.1021/ol061510m

data_1506155
_publ_section_title
;
 A tether controlled exo-selective trans-annular Diels-Alder (TADA)
 reaction.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3849
_journal_page_last               3851
_journal_paper_doi               10.1021/ol061510m
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29
_chemical_name_systematic
; 
(2R,3aR,5aR,7aS,10aS,10bS,10cR)-2-methoxy-2,3,3a,7a,8,
10a,10b,10c-octahydro-5aH-1,9-dioxa-
dicyclopenta[a,h]naphthalen-10-one
;
_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                   6.3696(2)
_cell_length_b                   7.2069(2)
_cell_length_c                   29.1029(10)
_cell_measurement_temperature    100(2)
_cell_volume                     1335.97(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0751
_diffrn_reflns_av_sigmaI/netI    0.0224
_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       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            43529
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0542P)^2^+0.3653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                1742
_reflns_number_total             1969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061510msi20060620_110318.cif
_cod_data_source_block           WOFE448
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1506155