Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 6, Pages 1911-1916Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo902615u
Keywords
-
Categories
Funding
- NNSFC [20672066, 30600779]
- Education Ministry of China [706003]
Ask authors/readers for more resources
A general method for the preparation of enantiopure 2-alkene- or 2-alkyne-containing chain substituted piperidines was established by using nonracemic Betti base as a chiral auxiliary. The key step is that the auxiliary residue was removed by a novel base-catalyzed N-debenzylation via a formation of o-quinone methide mechanism in stead of the traditional hydrogenolysis, by which the alkene or alkyne groups survived. By this method, ten 2-alkene- or 2-alkyne-containing chain substituted piperidines were prepared on the gram scale within a few hours. To demonstrate the efficiency of the method and the versatility of the product, total syntheses of natural alkaloids (+)-pelletierine, (-)-lasubine II, and (+)-cermizine C were achieved by using (S)-2-allyl-N-Boc-piperidine as a versatile building block.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available