The diastereoselective Mizoroki-Heck reaction of N-benzylpyrrolidines that incorporate a protected allylic alcohol moiety allows the synthesis of enantiomerically pure pyrrolo[1,2-b]isoquinolines, generating a tertiary stereocenter. The best results were obtained with the use of bulky phosphanes, as P(o-Tol)3. When a good leaving group, such as pivaloyl is used as a protecting group, the trans-10-vinyl substituted pyrroloisoquinoline (10S,10aS)-2a is obtained as the major diastereoisomer in moderate yield. On the other hand, when the allylic alcohol is protected as a silyl ether, the protected alcohol is retained, obtaining an enol ether, whichafter deprotection and reduction leads to the trans-10-hydroxymethyl substituted pyrrolisoquinoline (10S,10aS)-5, in enantiomerically pure form, with complete diastereoselectivity.
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Diastereoselective formation of tertiary stereocenters via Mizoroki-Heck reaction
Published:
04 December 2015
by MDPI
in MOL2NET'15, Conference on Molecular, Biomed., Comput. & Network Science and Engineering, 1st ed.
congress CHEMBIO.MOL-01: Org. Chem., Med. Chem., Pharm. Industry, & Mol. Biol., Congress, Paris, France-Galveston, USA, 2023., Rostock, Germany-Bilbao, Spain-Galveston, Texas, USA, 2015
Abstract:
Keywords: Palladium; diastereoselective Heck reaction; alkaloids; pyrrolo[1,2-b]isoquinolines