Asymmetric synthesis of 1-Boc-3- and 4-hydroxypyrrolidines

✍ Scribed by Yutaka Aoyagi; Robert M. Williams

• Book ID: 104208875
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 869 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00807-2

✦ Synopsis

Lewis Acid-mediated coupling reactions of (5R, 6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (2a) with aUylsilanes (3a-d) proceeded to give the coupling products (4a-b) with moderate to good stereoselectivity. The coupling products (4a-b) were effectively converted into 1-Boc-3and 4-hydroxypyrrolidines (8a, syn-b, and c).