A highly stereoselective sequential allylic transfer reaction of diene with diboronyl reagent and aldehydes promoted by nickel catalyst.
[reaction: see text] A new protocol for the sequential allylic transfer reaction of a diene with two aldehydes in the construction of cyclic systems containing four stereogenic centers is achieved in a one-pot operation. Reaction of the diene-alehyde 1 with aldehyde in the presence of the diboronyl reagent catalyzed by a nickel complex produces products 2 and 3 depending on reaction conditions in high levels of diastereoselectivity. Extension of this method to the synthesis of six-membered rings is also investigated.
Yu
Chan-Mo
CM
Department of Chemistry and Institute of Basic Sciences, Sungkyunkwan University, Suwon 440-746, Korea. cmyu@chem.skku.ac.kr
Youn
Jinsuop
J
Yoon
Seok-Keun
SK
Hong
Young-Tack
YT