ChemInform Abstract: Diastereoselective Ring Closing Metathesis Reactions: Synthesis of Bicyclic Diallylic Alcohols and Ethers.

✍ Scribed by Mark Lautens; Gregory Hughes

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199920080

✦ Synopsis

Diastereoselective Ring Closing Metathesis Reactions: Synthesis of Bicyclic Diallylic Alcohols and Ethers. -A novel class of bicyclic diallylic alcohols and ethers (II)/(III) is synthesized by ring closing metathesis of the tetraenes (I) in the presence of a benzylideneruthenium catalyst. The reaction affords primarily symmetric triene adducts like (X) or (XI) which undergo a recyclization to furnish the title bicyclic derivatives in cis-selectivity [except for the trans-diallylic alcohol (IIIb)]. Ring closing metathesis of the corresponding trienes (IV) proceeds with analogous diastereoselectivities. As shown for the derivative (VIII), bicyclic diallylic ethers can undergo Wittig rearrangement to give conjugated dienes. -(LAUTENS, MARK; HUGHES,