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Thioalkylation of enolates, II. – α-Thioalkylation of Zinc Enolates to α,α-Disubstituted Ketones

✍ Scribed by Groth, Ulrich ;Huhn, Thomas ;Richter, Norbert

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
640 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

An α‐alkylation of the 2‐methylcycloalkanones 1 and 4 at the higher substituted carbon can be achieved by thioalkylation of the corresponding zinc enolates with the α‐chlorosulfides 3. The desulfurization can be carried out with either Raney nickel or lithium in diethylamine for compounds which contain double or triple bonds.

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Thioalkylation of Enolates, IV. α-Alkyli
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✍ Arnecke, Ralf ;Groth, Ulrich ;Köhler, Thomas 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 490 KB

## Abstract An α‐alkylidation of cyclopentanone was achieved in two reaction steps in an overall yield of 20 to 79% via a zinc chloride‐catalyzed thioalkylation of the zinc enolate of methyl 2‐oxocyclopentanecarboxylate (3) and subsequent saponification/desulfurization of the β‐(phenylthio) ketone

Thioalkylation of Enolates, III. Stereos
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Stereoselective Formation of Quaternary
Stereoselective Formation of Quaternary Carbon Centers: Alkylation of α,α-Disubstituted Amide Enolates
✍ Jeffrey M. Manthorpe; James L. Gleason 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 97 KB

The stereoselective formation of quaternary carbon centers is one of the most challenging tasks in organic chemistry and can only be achieved using methods which employ some form of carbon ± carbon bond forming reaction. [1] One of the most straightforward methods for the formation of carbon ± carbo