Diastereoselektive Diels??Alder??Reaktionen mit α??Chlornitrososacchariden

…, FP Schmidtchen, R Prewo, A Vasella

Index: Braun, Heinz; Felber, Helena; Kresze, Guenter; Schmidtchen, Franz P.; Prewo, Roland; Vasella, Andrea Liebigs Annalen der Chemie, 1993 , # 3 p. 261 - 268

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Citation Number: 21

Abstract

The a-chloronitroso reagent 2 obtained from ribose via the lactone oxime 3 reacts with the dienes 6-10 at low temperature to give the chiral dihydrooxazines 11-16 in 63-96% yield and> 96% enantiomeric excess. The reagents 1 and 2 which are approximately mirror images in the vicinity of the chloronitroso function lead to opposite enantiomers of 11-16. The absolute configuration of the products was determined by chemical degradation and ...