Tetrahedron: Asymmetry

Synthesis and transformation of novel cyclic β-amino acid derivatives from (+)-3-carene

S Gyónfalvi, Z Szakonyi, F Fülöp

Index: Gyonfalvi, Szilvia; Szakonyi, Zsolt; Fueloep, Ferenc Tetrahedron Asymmetry, 2003 , vol. 14, # 24 p. 3965 - 3972

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Citation Number: 61

Abstract

The regio-and stereoselective addition of chlorosulfonyl isocyanate to (+)-3-carene 1 resulted in β-lactam 2, which was converted to N-Boc-β-amino acid 4, β-amino ester 7, and carboxamide derivatives 18 and 20 via N-Boc activation and mild ring opening. The corresponding β-amino ester 7 was transformed to 2-thioxopyrimidin-4-one 11 and 2, 4- pyrimidinedione 13. LAH reduction of 5 and 7 resulted in amino alcohols 6 and 8. The ...