An efficient method for the synthesis of enantiopure 2,3-anti-propionate aldols involving a 3,5-syn- or anti-diol subunit through chiral borane-mediated enantioselective aldol reaction coupled with radical reduction

✍ Scribed by Syun-ichi Kiyooka; Kazi A Shahid

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 182 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00234-3

✦ Synopsis

2,3-anti-Propionate aldols involving a 3,5-syn-or anti-diol subunit, versatile enantiopure segments available for macrolide synthesis, were prepared by a chiral oxazaborolidinone-promoted asymmetric aldol reaction with 2-bromo-1-ethoxy-2-methyl-1-trimethylsiloxyethene and the following highly anti-preferential radical debromination.