Boron-mediated aldol reactions of ethyl α-(N,N)-dibenzylamino ketones: control of enolisation geometry and aldehyde π-facial selectivity

✍ Scribed by Ian Paterson; Angela C Mackay

• Book ID: 104232027
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 157 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01982-7

✦ Synopsis

The boron-mediated aldol reactions of a range of chiral a-(N,N)-dibenzylamino ketones with aldehydes can be controlled to provide stereodefined adducts. Complementary induction can be achieved with c Hex 2 BCl/Me 2 NEt leading to preferential formation of the 1,2-anti-2,4-syn adducts, while Bu 2 BOTf/ i Pr 2 NEt provides 1,2-syn-2,4-anti adducts.