𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A stereoselective synthesis of Z)-α,β-disubstituted acrylates

✍ Scribed by Masayuki Shimagaki; Manabu Shiokawa; Kazunori Sugai; Tomoko Teranaka; Tadashi Nakata; Takeshi Oishi

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
229 KB
Volume
29
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Sumary : A new route for (Z)-u.B-disubstituted acrylate is described which is made up of 1) stereoselective reduction of ketones 3 and 2) conversion of the resulting syn-2 into (Z)-1. Developement of a stereoselective method for the synthesis of (Z)-a,B-disubstituted acrylate 1 has attracted considerable attention, since the Wittig type reaction proceeding through stabilized ylides prefer to afford the more stable (E)-isomer. Recently, it was reported that the long-desired (Z)-isomer could be synthesized effectively by the Horner-Emmons reaction provided phosphonoester reagent was properly designed.l However. in view of the importance of these moieties in natural product synthesis. it seemed worthwhile to explore another practical approach.

We now report that (Z)-1 could be synthesized effectively by the

📜 SIMILAR VOLUMES

A stereoselective synthesis of β,γ-disub
A stereoselective synthesis of β,γ-disubstituted allylic alcohols of z-configuration
✍ Mitsuhisa Tamura; Gohu Suzukamo 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 190 KB

Reaction of alkyllithiums 1 with isoprene epoxide 2 gives B,y-disubstituted allylic alcohols 2 of Z-configuration. The reaction of \*-lithiotricyclene as alkyllithium gives o-santalol 5, which is one of the main constituents in East Indian sandalwood oil.

Stereoselective Synthesis of (Z)-α-Aryl-
Stereoselective Synthesis of (Z)-α-Aryl-α,β-unsaturated Esters.
✍ Neelakandha S. Mani; Christopher M. Mapes; Jiejun Wu; Xiaohu Deng; Todd K. Jones 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 21 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.