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Communication | Regular issue | Vol 51, No. 7, 1999, pp.1509-1512
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8580
A Versatile Approach to trans-1,3-Disubstituted Tetrahydro-β-carbolines Using Oxazinanes

Kamajit Singh* and Prasant K. Deb

*Department of Applied Chemical Sciences&Technology, Guru Nanak Dev University, Amritsar-143 005, Punjab, India


Under the conditions of thermodynamic control, the diastereoselectivity of the reaction between tryptophan esters and oxazinanes (carbonyl equivalents) can be controlled by incorporating Nb-benzyl substituents; the reaction proceeds in essentially quantitative yield and with trans-diastereoselectivity.