Stereoelectronic versus steric tuning in the prins cyclization reaction: synthesis of 2,6-trans pyranyl motifs

Xu-Hong Hu; Feng Liu; Teck-Peng Loh

doi:10.1021/ol900196w

Stereoelectronic versus steric tuning in the prins cyclization reaction: synthesis of 2,6-trans pyranyl motifs

Org Lett. 2009 Apr 16;11(8):1741-3. doi: 10.1021/ol900196w.

Authors

Xu-Hong Hu¹, Feng Liu, Teck-Peng Loh

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

PMID: 19301864
DOI: 10.1021/ol900196w

Abstract

The use of carboalkoxyl allenic alcohol for the efficient synthesis of pyranyl motifs via Prins cyclization is described. This method provides easy access to 2,6-trans dihydropyrans in good yield and high diastereoselectivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes / chemistry*
Catalysis
Cyclization
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry
Stereoisomerism

Substances

Alkadienes
Pyrans
propadiene