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

✍ Scribed by Masako Uchikawa; Takeshi Hanamoto; Tsutomu Katsuki; Masaru Yamaguchi

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 244 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85007-8

✦ Synopsis

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 stereochemically well-understood C3,33sigmatropic rearrangement, its C2,33counterpart had not found its proper position in synthetic control until recently when extensive studies by Nakai et al. 1) disc?osed that this type of reaction was also very useful for acyclic stereocontrol in the synthesis of alcohols.