Asymmetric synthesis using a new chiral β-functionalized allylboronate derived from endo-2-phenyl-exo-2,3-bornanediol: Preparation and reactions with aldehydes

✍ Scribed by Isabelle Chataigner; Jacques Lebreton; Françoise Zammattio; Jean Villiéras

• Book ID: 104257070
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 207 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00708-9

✦ Synopsis

The allylboron reagent 4 prepared .from endo-2-phenyl-exo-2,3-bornanediol reacts with achiral aldehydes to give homoallylic alcohols in good yields and high enantioselectivity (70-85% ee). This new reagent also exhibits good levels of matched and mismatched diastereoselection in reaction with chiral aldehydes. A mechanism is proposed to explained the high regio and stereoselectivi~ of this carboalkoxyaUylboration reaction.