Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions

✍ Scribed by Susan M. Lait; Masood Parvez; Brian A. Keay

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 277 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00051-x

✦ Synopsis

A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-1-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo-and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl 3 -catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5.