Organocatalytic Asymmetric Robinson Annulation of α,β-Unsaturated Aldehydes: Applications to the Total Synthesis of (+)-Palitantin.

Content Provider	Semantic Scholar
Author	Bor-Cherng Tseng, Hsing-Chang Huang, Guo-Fong Su, Cheng-Feng Liao, J.
Copyright Year	2007
Abstract	The highly enantioselective organocatalytic Robinson annulation of α,β-unsaturated aldehydes was achieved, catalyzed by l-proline and trialkylamines and providing the formal [4 + 2] cycloaddition adducts. Additionally, in some examples in the catalysis with diarylpyrrolinol silyl ethers, the reactions afforded the [4 + 2] adducts with high enantioselectivity (>99.5% ee). The structure of the adduct, obtained from the reaction of 3-methylbut-2-enal and (E)-3-(2-nitrophenyl)acrylaldehyde, was confirmed by X-ray analysis. The absolute configurations of some [4 + 2] cycloadducts were investigated, and the methodology was applied in the synthesis of (+)-palitantin.
Starting Page	8459
Ending Page	8471
Page Count	13
File Format	PDF HTM / HTML
DOI	10.1021/jo701477v
Volume Number	72
Alternate Webpage(s)	http://www.chem.ccu.edu.tw/~bch/Publications/PubRefFiles/2007%20JOC%208459.pdf
Alternate Webpage(s)	https://doi.org/10.1021/jo701477v
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article