Aldol reactions in polypropionate synthesis: High π-face selectivity of enol borinates from α-chiral methyl and ethyl ketones under substrate control

✍ Scribed by Ian Paterson; Jonathan M. Goodman; Masahiko Isaka

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 277 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93440-9

✦ Synopsis

Use of (c-CgH11)2BCl in the anti-selective aldol reaction of the u-chiral ethylketone 2 leads to high stercoselectivity (>94%) for the 1,2-anti-2,4-anti isomer 7. The related u-chiral methylketone aldol reaction, 8 --t 9, proceeds with 84-93% diastereoselectivity for a range of boron reagents.