Diastereoselective Yang Photocyclization Reactions in Solution. Synthesis of Enantiopure Azetidin-3-ol Derivatives
- 19 January 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (4) , 1408-1416
- https://doi.org/10.1021/jo0481497
Abstract
Chiral 2-acyl-3-allyl- or 2-acyl-3-benzyl-substituted perhydro-1,3-benzoxazines readily cyclized under irradiation to azetidin-3-ol derivatives. The diastereoselectivity of the cyclization is dependent on the nature of the substituents at the nitrogen atom. N-allyl-substituted derivatives yielded only two of the four possible diastereomers in moderate to good diastereomeric excess. The cyclization of N-benzyl derivatives was totally diastereoselective leading to a single diastereomer. The elimination of the menthol appendage lead to enantiopure 2,3-disubstituted azetidin-3-ol derivatives.Keywords
This publication has 81 references indexed in Scilit:
- Preorganization of Achiral Molecules for Asymmetric Synthesis through Crystallization‐Induced Immobilization in Homochiral ConformationsAngewandte Chemie International Edition in English, 2003
- Intermolecular hydrogen binding of a chiral host and a prochiral imidazolidinone: enantioselective Norrish–Yang cyclisation in solutionChemical Communications, 2001
- Reactivity and Efficiency of Singlet- and Triplet-Excited States in Intermolecular Hydrogen Abstraction ReactionsJournal of the American Chemical Society, 1996
- Zeolite as a host for chiral inductionChemical Communications, 1996
- Ring-opening of 3-benzyloxyazetidinium salts with organophosphorus nucleophiles Application to the synthesis of poly functional aminophosphonic acids analoguesTetrahedron Letters, 1995
- Intersystem Crossing in Triplet 1,4-Biradicals: Conformational Memory Effects on the Stereoselectivity of Photocycloaddition ReactionsAccounts of Chemical Research, 1994
- Photoreactivity of n,π* Excited States of Alkyl KetonesAnnual Review of Physical Chemistry, 1970
- Photoreduction of acetone by tributylstannaneJournal of the American Chemical Society, 1967
- The Lifetime of Triplet Acetone in Solution1Journal of the American Chemical Society, 1966
- Hydrogen Abstraction Reactions by the Triplet States of Ketones1Journal of the American Chemical Society, 1965