ChemInform Abstract: Asymmetric One‐Pot Four‐Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether.

Abstract

Substituted tetrahydropyrans are synthesized with excellent enantioselectivity. In the first step, aldehydes and nitroalkanes undergo Michael addition followed by subsequent Henry and acetalization. This reaction tolerates various functional groups whereby, diastereoselectivity is much higher for aromatic derivatives than for aliphaticones. As is shown for (XV), it is also possible to perform a four-component coupling under similar conditions with subsequent allylation. -(ISHIKAWA, H.; SAWANO, S.; YASUI, Y.; SHIBATA, Y.; HAYASHI*, Y.; Angew. Chem., Int. Ed. 50 (2011) 16, 3774-3779, http://dx.doi.org/10.1002/anie.201005386 ; Dep. Ind. Chem., Fac. Eng., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan; Eng.) -S. Adam