A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones

Hua Wang, Brian J. Shuhler, Ming Xian

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

(Chemical Equation Presented) A concise synthesis of 2,6-disubstituted dihydropyranones was developed. This sequence is based on the Smith three-component dithiane linchpin coupling strategy. By simply switching the order of epoxide addition in the linchpin coupling step, two analogous dihydropyranones were prepared in good yield from the same starting materials. This sequence allows for considerable flexibility in the nature of R1 and R2 groups, which facilitates the preparation of a diverse array of 2,6-disubstituted dihydropyranones.

Original languageEnglish (US)
Pages (from-to)4280-4283
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number11
DOIs
StatePublished - May 25 2007
Externally publishedYes

Fingerprint

Epoxy Compounds
dithiane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones. / Wang, Hua; Shuhler, Brian J.; Xian, Ming.

In: Journal of Organic Chemistry, Vol. 72, No. 11, 25.05.2007, p. 4280-4283.

Research output: Contribution to journalArticle

Wang, Hua ; Shuhler, Brian J. ; Xian, Ming. / A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 11. pp. 4280-4283.
@article{29a699b8c7a54b2b90abcc94ca446e2c,
title = "A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones",
abstract = "(Chemical Equation Presented) A concise synthesis of 2,6-disubstituted dihydropyranones was developed. This sequence is based on the Smith three-component dithiane linchpin coupling strategy. By simply switching the order of epoxide addition in the linchpin coupling step, two analogous dihydropyranones were prepared in good yield from the same starting materials. This sequence allows for considerable flexibility in the nature of R1 and R2 groups, which facilitates the preparation of a diverse array of 2,6-disubstituted dihydropyranones.",
author = "Hua Wang and Shuhler, {Brian J.} and Ming Xian",
year = "2007",
month = "5",
day = "25",
doi = "10.1021/jo070346t",
language = "English (US)",
volume = "72",
pages = "4280--4283",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "11",

}

TY - JOUR

T1 - A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones

AU - Wang, Hua

AU - Shuhler, Brian J.

AU - Xian, Ming

PY - 2007/5/25

Y1 - 2007/5/25

N2 - (Chemical Equation Presented) A concise synthesis of 2,6-disubstituted dihydropyranones was developed. This sequence is based on the Smith three-component dithiane linchpin coupling strategy. By simply switching the order of epoxide addition in the linchpin coupling step, two analogous dihydropyranones were prepared in good yield from the same starting materials. This sequence allows for considerable flexibility in the nature of R1 and R2 groups, which facilitates the preparation of a diverse array of 2,6-disubstituted dihydropyranones.

AB - (Chemical Equation Presented) A concise synthesis of 2,6-disubstituted dihydropyranones was developed. This sequence is based on the Smith three-component dithiane linchpin coupling strategy. By simply switching the order of epoxide addition in the linchpin coupling step, two analogous dihydropyranones were prepared in good yield from the same starting materials. This sequence allows for considerable flexibility in the nature of R1 and R2 groups, which facilitates the preparation of a diverse array of 2,6-disubstituted dihydropyranones.

UR - http://www.scopus.com/inward/record.url?scp=34249807049&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34249807049&partnerID=8YFLogxK

U2 - 10.1021/jo070346t

DO - 10.1021/jo070346t

M3 - Article

C2 - 17447817

AN - SCOPUS:34249807049

VL - 72

SP - 4280

EP - 4283

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 11

ER -