✦ LIBER ✦

Highly stereoselective preparation of nitro olefins and nitro dienes by the addition-elimination of copper-zinc organometallics to β-alkylthio and β-phenylsulfonyl nitro olefins

✍ Scribed by Carole Retherford; Paul Knochel

Publisher: Elsevier Science
Year: 1991
Tongue: French
Weight: 351 KB
Volume: 32
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)79462-7

No coin nor oath required. For personal study only.

✦ Synopsis

The addition-elimination of copper-zinc organometallicsRCu(CN)ZnX to (E)-1-nitro-2-phenylsulfonyl ethylene 2a gave highlyfunctionalizedpure (E) nitro olefns and stereoselectively (IE, 3E) and (IE, 3Z)-I-nitrodienes in excellent yields. J%Alkylthio nitro olejks such as 2-ethylthio-1 -nitro-I-cyclohexene 2b and 2,2-dimethylthio-l-nitroethylene 12 were found to have a similar behavior. This methodology allowed an expeditive preparation of the triene 5 which underwent an extremely mild silica gel-catalyzed, stereospecifc Diels-Alder cyclization.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of (E)-Ni

ChemInform Abstract: Synthesis of (E)-Nitro Olefins by Copper Mediated Addition—Elimination Reaction of Organometallics to 2-Nitro-1-phenylthiopropene.

✍ P. STANETTY; M. KREMSLEHNER 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 2 views

Highly Stereoselective Oxy-Michael Addit

Highly Stereoselective Oxy-Michael Additions to α,β-Disubstituted Nitro Olefins: Asymmetric Synthesis of Pseudo-Norephedrine Derivatives and THP* Protected α-Hydroxy Ketones.

✍ David J. Buchanan; Darren J. Dixon; Felix A. Hernandez-Juan 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 23 KB 👁 1 views