✦ LIBER ✦

A practical new asymmetric synthesis of (2S,3S)- and (2R,3R)-3-hydroxyleucine

✍ Scribed by Karl J. Hale; Soraya Manaviazar; Vern M. Delisser

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 552 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85384-9

No coin nor oath required. For personal study only.

✦ Synopsis

Abstmctz A convenient new asymmetric synthesis of both enaatiomcrs of eryrhro-3-hydroxylcuciae is desctibed. The key steps involve Sharpless asymmetric dihydroxylation (AD) of a&unsaturated ester 3, cyclic sulphate formation from the resulting diol, SNZ reaction with sodium azide, deesterification with aqueous sodium hydroxide, and hydrogenolysis. Utilising this route, (2S,3S)-(+> 3-hydroxyleucine (1) was obtained in 97% ee and 67% overall yield; the (2R,3R)-(-)-enantiomer was isolated in 92% ee and 57% overall yield.

📜 SIMILAR VOLUMES

A practical stereoselective synthesis of

A practical stereoselective synthesis of (2S, 3S)-3-hydroxyleucine

✍ Lorenzo Williams; Zhongda Zhang; Xiaobin Ding; Madeleine M. Joullié 📂 Article 📅 1995 🏛 Elsevier Science 🌐 French ⚖ 185 KB

An efficient asymmetric synthesis of (2S

An efficient asymmetric synthesis of (2S,3S)- and (2R,3R)-β-hydroxyornithine

✍ Duane E DeMong; Robert M Williams 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 80 KB

ChemInform Abstract: Efficient Enantiose

ChemInform Abstract: Efficient Enantioselective Synthesis of (2R,3R)- and (2S,3S)-3-Hydroxyleucines and Their Diastereomers Through Dynamic Kinetic Resolution.

✍ Kazuishi Makino; Naoki Okamoto; Osamu Hara; Yasumasa Hamada 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 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

Asymmetric synthesis of (2S,3S)- and (2S

Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-methylsulfanylmethyl-pyrrolidine-2-carboxylic acids

✍ Philippe Karoyan; Gérard Chassaing 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 547 KB

The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCI, the zinc--copper derivative was reacted with S-methyl methanesulfonothioate leading in a "one-pot" procedure, to N-(0t-meth

Asymmetric synthesis of(-)-(2R,3R,6S)-ir

Asymmetric synthesis of(-)-(2R,3R,6S)-irnigaine

✍ Nan Ma; Da-Wei Ma 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 292 KB 👁 1 views

A new practical synthesis of (2S,3R,4R,5

A new practical synthesis of (2S,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine

✍ Wei Zou; Walter A. Szarek 📂 Article 📅 1993 🏛 Elsevier Science 🌐 English ⚖ 317 KB