Stereoselective Synthesis of cis- and trans-2,5- Disubstituted Tetrahydrofurans

Chem. J. Chinese Universities ›› 2003, Vol. 24 ›› Issue (5): 831.

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Stereoselective Synthesis of cis- and trans-2,5- Disubstituted Tetrahydrofurans

SHI Hong-Xin¹, LIU Hua-Zhang¹, Bloch R², Mandville G.², LIN Hui³

1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China;
2. Universite de Paris-Sud, ICMO 91405, Orsay Cedex, France;
3. Department of Chemistry, Institute of Science, Zhejiang University, Hangzhou 310012, China

Received:2002-04-30 Online:2003-05-24 Published:2003-05-24

Abstract

Abstract: Ageneral route to either cis- or trans-2,5-disubstituted tetrahydrofurans was described by using the nucleophilic addition of organolithium derivatives to tricyclic lactones, followed by a highly stereocon-trolled acid-assisted reduction with sodium cyanoborohydride of the hemiketals formed. The stereoselec-tivity observed can be rationalized by the preferential approach of the hydride on the less hindered face of an oxonium ion intermediate. The cis- or trans-2, 5-disubstituted tetrahydrofurans were provided by the hot decomposition and then hydrogenation of tricycle compounds produced.

Key words: Stereoselectivity, Oxygen heterocycles, Disubstituted tetrahydrofuran, Chirality

CLC Number:

O641.6

TrendMD:

SHI Hong-Xin, LIU Hua-Zhang, Bloch R, Mandville G., LIN Hui. Stereoselective Synthesis of cis- and trans-2,5- Disubstituted Tetrahydrofurans[J]. Chem. J. Chinese Universities, 2003, 24(5): 831.

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Stereoselective Synthesis of cis- and trans-2,5- Disubstituted Tetrahydrofurans

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