✦ LIBER ✦

Stereochemistry of [2,3]Sigmatropic Rearrangements

✍ Scribed by Prof. Dr. Reinhard W. Hoffmann

Publisher: John Wiley and Sons
Year: 1979
Tongue: English
Weight: 810 KB
Volume: 18
Category: Article
ISSN: 0044-8249
DOI: 10.1002/anie.197905633

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Stereoselective synthesis is attracting more and more attention. Successful stereoselective syntheses require the availability of reactions of known stereochemistry which give maximum yields of the desired products. This is particularly so with reactions proceeding via cyclic transition states. Of these, the stereochemistry of [3,3]sigmatropic processes has long been known. This article now summarizes the factors determining the stereoselectivity of [2,3]sigmatropic rearrangememts.

📜 SIMILAR VOLUMES

Stereochemistry of a [2,3] sigmatropic a

Stereochemistry of a [2,3] sigmatropic allyl-sulfoxide/allyl sulfenate rearrangement

✍ R.W. Hoffmann; R. Gerlach; S. Goldmann 📂 Article 📅 1978 🏛 Elsevier Science 🌐 French ⚖ 207 KB

3,3lSigmatropic rearrangements follow a well defined stereochemistry') and lend themselves for asymmetric syntheses 2) . Much less is known about the stereoche-3) mistry of [2,3]sigmatropic rearrangements , which also show high stereoselecti-vities4', 5) being even stereospecific in some cases . We

On the stereochemistry of anion-accelera

On the stereochemistry of anion-accelerated [1,3]-sigmatropic rearrangement of 2-vinylcyclobutanols

✍ Se-Ho Kim; Sung Yun Cho; Jin Kun Cha 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 83 KB

Stereochemical studies on the oxyanion-accelerated [1,3]-sigmatropic rearrangement reactions of nonracemic cis-and trans-2-(1-cyclohexenyl)cyclobutanols are described. Epimerization of cis-2-(1-cyclohexenyl)cyclobutanol to the trans-isomer at -20°C was found to proceed with predominant retention of

[2,3]-Wittig sigmatropic rearrangement o

[2,3]-Wittig sigmatropic rearrangement of crotyl propargyl ether system. An emerging tool for control of acyclic stereochemistry

✍ Kōichi Mikami; Ken-Ichi Azuma; Takeshi Nakai 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 644 KB

Investigation of the stereochemistry of

Investigation of the stereochemistry of the [3.3]-sigmatropic rearrangement of the sp-isomer of 2-allylthio-5-acetyl-6-methyl-4-(2-nitrophenyl)-3-cyano-1,4-dihydropyridine

✍ V. N. Nesterov; L. A. Rodinovskaya; A. M. Shestopalov; Yu. T. Struchkov 📂 Article 📅 1997 🏛 Springer US 🌐 English ⚖ 515 KB

ChemInform Abstract: Investigation of th

ChemInform Abstract: Investigation of the Stereochemistry of the [3.3]Sigmatropic Rearrangement of the 2-Allylthio-5-acetyl-6-methyl-4- (2-nitrophenyl)-3-cyano-1,4-dihydropyridine sp-Isomer.

✍ V. N. NESTEROV; L. A. RODINOVSKAYA; A. M. SHESTOPALOV; YU. T. STRUCHKOV 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

[2,3]-Sigmatropic Rearrangements of Dide

[2,3]-Sigmatropic Rearrangements of Didehydropiperidinium Ylids.

✍ J. B. Sweeney; Ali Tavassoli; Neil B. Carter; Jerome F. Hayes 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 189 KB 👁 2 views