✦ LIBER ✦

Concomitant [2,3]-sigmatropic rearrangement of allylic sulfilimines and intramolecular N-alkylation. Synthesis of 2-vinyl substituted cyclic amines

✍ Scribed by Roland E. Dolle; Chun-Sing Li; Antony N. Shaw

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 222 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80785-1

No coin nor oath required. For personal study only.

✦ Synopsis

Allylic phenyl and methyl sulfides bearing a strategically positioned electrophilic center have been shown to undergo concomitant C2,31-sigmatropic rearrangement and intramolecular N-alkylation upon oxidative conversion to allylic sulfilimines and treatment with aqueous base. This one-pot transformation leads to the title class of compounds in good yield. The development of synthetic methodology permitting the regio-and stereocontrolled construction of 2-substituted and 2,2_disubstituted cyclic amines remains an active area of research2 and in this Letter we communicate a novel stratagem for preparing 2-functionalized nitrogen heterocycles.

📜 SIMILAR VOLUMES

ChemInform Abstract: N-Alkylation and [2

ChemInform Abstract: N-Alkylation and [2,3]-Sigmatropic Rearrangement of N-Allyl α-Amino Esters.

✍ I. COLDHAM; M. L. MIDDLETON; P. L. TAYLOR 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

ChemInform Abstract: Asymmetric Copper-C

ChemInform Abstract: Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides.

✍ Douglas W. McMillen; Norbert Varga; Beth Ann Reed; Claudia King 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 2 views

Rearrangements of silyl- and stannyl-sub

Rearrangements of silyl- and stannyl-substituted diallyl ethers: competition between the allyl-vinyl ether rearrangement and the [2,3] Wittig sigmatropic rearrangement

✍ T.N. Mitchell; F. Gießelmann; K. Kwetkat 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 448 KB

ChemInform Abstract: 1,2-Asymmetric Indu

ChemInform Abstract: 1,2-Asymmetric Induction in a New Tandem of (3,3)-Sigmatropic Rearrangement of Allylic Thiocyanates and Intramolecular Amine to N=C= S Group.

✍ M. MARTINKOVA; J. GONDA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

Synthesis and Lewis acid catalyzed Clais

Synthesis and Lewis acid catalyzed Claisen rearrangement of 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers

✍ Hannes Helmboldt; Martin Hiersemann 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 245 KB

Allyl vinyl ethers containing an acceptor function in the 2-position are useful substrates for the Lewis acid-catalyzed Claisen rearrangement. The first synthesis of acyclic 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers is reported. The Lewis acid catalyzed Claisen rearrangement of these ally

1,2-Asymmetric induction in a new tandem

1,2-Asymmetric induction in a new tandem of (3,3)-sigmatropic rearrangement of allylic thiocyanates and intramolecular amine addition to NCS group

✍ Miroslava Martinková; Jozef Gonda 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 202 KB