Asymmetric acylation of carboxamides having trans-2,5-bis(methoxymethoxymethyl)pyrrolidine moiety as a chiral auxiliary and stereoselective reduction of the resulting 2-alkyl-3-oxoamides

Asymmetric [2,3]wittig rearrangement of

Asymmetric [2,3]wittig rearrangement of 2′-alkenyloxyacetamide bearing trans-2,5-bis(methoxymethoxymethyl)pyrrolidine moiety as a chiral auxiliary

✍ Masako Uchikawa; Takeshi Hanamoto; Tsutomu Katsuki; Masaru Yamaguchi 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 244 KB

C2,33Wittig rearrangement of (2S,SS)-N-(alkenyloxyacetyl)-2,5-bis-(methoxymethoxymethyl)pyrrolidine enolate was Studied and zirconium enolates of the corresponding (E)-alkenyloxyacetyl compounds were found to rearrange with high syn-diastereo and diastereoface selection. In contrast to the stereoche