Preorganization of achiral molecules for asymmetric synthesis through crystallization-induced immobilization in homochiral conformations

Angewandte Chemie - International Edition

Volumn 42, Issue 32, 2003, Pages 3775-3777

  Patrick, Brian O ^a   Scheffer, John R ^a   Scott, Carl ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Asymmetric synthesis; Crystal engineering; Photochemistry; Solid state reactions; Topochemistry

Indexed keywords

AMINES; CARBOXYLIC ACIDS; CRYSTALLIZATION; GAMMA RAYS; SALTS;

ENANTIOMERS;

PHOTOCHEMICAL REACTIONS;

ALCOHOL DERIVATIVE; CYCLOBUTANOL; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONFORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; ENANTIOSELECTIVITY; IMMOBILIZATION; IRRADIATION; PHOTOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0041863968     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351609     Document Type: Article

References (24)

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18. 1,4-Hydroxybiradical ring closure involving retention of configuration at the hydroxyl-bearing carbon has been noted previously and appears to be a general feature of Yang photo-cyclization reactions conducted in the crystalline state. See for example A. D. Gudmundsdottir, T. J. Lewis, L. H. Randall, S. J. Rettig, J. R. Scheffer, J. Trotter, C.-H. Wu, J. Am. Chem. Soc. 1996, 118, 6167; M. Leibovitch, G. Olovsson, J. R. Scheffer, J. Trotter, J. Am. Chem. Soc. 1998, 120, 12755.
19. 1,4-Hydroxybiradical ring closure involving retention of configuration at the hydroxyl-bearing carbon has been noted previously and appears to be a general feature of Yang photo-cyclization reactions conducted in the crystalline state. See for example A. D. Gudmundsdottir, T. J. Lewis, L. H. Randall, S. J. Rettig, J. R. Scheffer, J. Trotter, C.-H. Wu, J. Am. Chem. Soc. 1996, 118, 6167; M. Leibovitch, G. Olovsson, J. R. Scheffer, J. Trotter, J. Am. Chem. Soc. 1998, 120, 12755.
20. Interestingly, the diastereoselectivity of the solution phase photoreaction is identical to that observed in the crystalline state. One explanation of this result is that, even in solution, rotation about the C7-carbonyl carbon bond in the initially formed biradical is slow relative to closure owing to unfavorable steric interactions developed between the aryl and methyl groups. In addition, the biradical (a triplet) may be formed in a conformation in which intersystem crossing to the singlet and closure is faster than rotation. For examples in which geometry-dependent intersystem crossing is thought to control the stereochemistry of 1,4-biradical closure, see A. G. Griesbeck, H. Heckroth, J. Am. Chem. Soc. 2002, 124, 396, and references therein.
21. See for example, V. Buchholz, V. Enkelmann, Mol. Cryst. Liq. Cryst. 1998, 313, 309; K. Novak, V. Enkelmann, G. Wegner, K. B. Wagnener, Angew. Chem. 1993, 105, 1678; Angew. Chem. Int. Ed. Engl. 1993, 32, 1614. For a counter example, see K. Honda, Bull. Chem. Soc. Jpn. 2002, 75, 2383.
22. See for example, V. Buchholz, V. Enkelmann, Mol. Cryst. Liq. Cryst. 1998, 313, 309; K. Novak, V. Enkelmann, G. Wegner, K. B. Wagnener, Angew. Chem. 1993, 105, 1678; Angew. Chem. Int. Ed. Engl. 1993, 32, 1614. For a counter example, see K. Honda, Bull. Chem. Soc. Jpn. 2002, 75, 2383.
23. See for example, V. Buchholz, V. Enkelmann, Mol. Cryst. Liq. Cryst. 1998, 313, 309; K. Novak, V. Enkelmann, G. Wegner, K. B. Wagnener, Angew. Chem. 1993, 105, 1678; Angew. Chem. Int. Ed. Engl. 1993, 32, 1614. For a counter example, see K. Honda, Bull. Chem. Soc. Jpn. 2002, 75, 2383.
24. See for example, V. Buchholz, V. Enkelmann, Mol. Cryst. Liq. Cryst. 1998, 313, 309; K. Novak, V. Enkelmann, G. Wegner, K. B. Wagnener, Angew. Chem. 1993, 105, 1678; Angew. Chem. Int. Ed. Engl. 1993, 32, 1614. For a counter example, see K. Honda, Bull. Chem. Soc. Jpn. 2002, 75, 2383.