Molecular mechanics-assisted crystal engineering of solid state photoreactions: Application to the Yang photocyclization of α-1- norbornylacetophenone derivatives

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1141-1144

  Botoshansky, Mark ^a   Braga, Dario ^b   Kaftory, Menahem ^a   Maini, Lucia ^b   Patrick, Brian O ^c   Scheffer, John R ^c   Wang, Keyan ^c  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Asymmetric induction; Crystal engineering; Ionic chiral auxiliaries; Solid state photochemistry; X ray crystallography; Yang photocyclization

Indexed keywords

ACETOPHENONE DERIVATIVE; CARBONYL DERIVATIVE;

ARTICLE; CONFORMATION; CRYSTAL; CRYSTALLIZATION; CYCLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MOLECULAR DYNAMICS; PHOTOREACTIVITY; SOLID STATE;

EID: 12344336650     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.090     Document Type: Article

References (28)

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25. Diastereomers 3b and 5b were differentiated by the presence in 3b (and the lack in 5b) of an NOE interaction between the methine hydrogen on the four-membered ring and the ortho hydrogens on the aromatic ring; diastereomers 4b and 6b were differentiated similarly
26. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 248953 (salt 1c), CCDC 248954 (salt 2c) and CCDC 248955 (photoproduct 4b). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk)
27. 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 photocyclization 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, and C.-H. Wu J. Am. Chem. Soc. 118 1996 6167
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