Tetrahedron: Asymmetry

Synthesis and transformations of enantiomeric 1, 2-disubstituted monoterpene derivatives

Z Szakonyi, T Martinek, A Hetényi, F Fülöp

Index: Szakonyi, Zsolt; Martinek, Tamas; Hetenyi, Anasztazia; Fueloep, Ferenc Tetrahedron Asymmetry, 2000 , vol. 11, # 22 p. 4571 - 4579

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Citation Number: 50

Abstract

Regio-and stereospecific addition of chlorosulfonyl isocyanate to (+)-and (−)-α-pinene 1 resulted in enantiomerically pure β-lactams 2, which were converted to enantiomeric β- amino esters 3 and 1, 3-amino alcohols 4 and 6 with ee> 99%. The resulting 1, 3- difunctional compounds 3, 4 and 6 were transformed to fused saturated 1, 3-heterocycles such as tetrahydro-1, 3-oxazines 7 and 9, 2, 4-pyrimidinedione 11 and 2-thioxopyrimidin-4 ...