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A diastereoselective radical cyclisation approach to pyroglutamates

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JournalTetrahedron Letters
DatePublished - 20 Jan 1997
Issue number3
Volume38
Number of pages4
Pages (from-to)491-494
Original languageEnglish

Abstract

The 5-endo radical cyclisation of pyruvic acid derived dehydroalanines which contain chiral ester auxiliaries is reported. Cyclisation of the menthol ester derivative using Bu(3)SnH at 80 degrees C proceeded with low diastereoselectivity (1.75:1) but the selectivity could be increased to 6:1 on cyclisation of the corresponding 8-phenylmethyl ester at 20 degrees C. Copyright (C) 1996 Elsevier Science Ltd

    Research areas

  • ALPHA-AMINO-ACIDS, ASYMMETRIC INDUCTION, ENANTIOSELECTIVE SYNTHESES, LEWIS-ACID, CYCLIZATION, ESTERS, DEHYDROALANINE, AMIDES, STEREOSELECTIVITY, ORGANOBORANES

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