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Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals

✍ Scribed by Ian Paterson; Gordon J Florence

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
180 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with high levels of 1,4-stereoinduction arising from the g-substituent. Reagent control from (+)-Ipc 2 BCl can be used eectively to overturn this substrate bias, thus enabling the stereocontrolled formation of (+)-discodermolide (1) and related analogues 15±18.

📜 SIMILAR VOLUMES

ChemInform Abstract: A Practical Synthes
ChemInform Abstract: A Practical Synthesis of (+)-Discodermolide and Analogues: Fragment Union by Complex Aldol Reactions.
✍ Ian Paterson; Gordon J. Florence; Kai Gerlach; Jeremy P. Scott; Natascha Sereini 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 25 KB 👁 2 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

Auxiliary structure and asymmetric induc
Auxiliary structure and asymmetric induction in the “Mukaiyama-aldol” reactions of chiral silyl ketene acetals
✍ Cesare Gennari; Francesco Molinari; PierGiorgio Cozzi; Ambrogio Oliva 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 244 KB

## A variety of chiral auxiliaries R*OH were prepared ana' tested for levels of asymmetric induction control in the 'Mukaiyama-ala'& reaction of chiral siiyl ketene acetals. Structural features required for high levels of control are discussed.