Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers

D-Threonine-L-tert-leucine-derived bifunctional phosphine, Cat. 11, catalyzed highly enantioselective [3+2] annulation of maleimides with allenes has been disclosed, allowing the synthesis of optically active functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers in good t...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2012-01, Vol.48 (7), p.970-972
Main Authors: Zhao, Qianyi, Han, Xiaoyu, Wei, Yin, Shi, Min, Lu, Yixin
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Asymmetry
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Catalysis
Chemical reactions
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Dipeptides - chemistry
Maleimides - chemistry
Optical activity
Organic chemistry
Phosphines
Phosphines - chemistry
Stereoisomerism
Synthesis
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Summary:D-Threonine-L-tert-leucine-derived bifunctional phosphine, Cat. 11, catalyzed highly enantioselective [3+2] annulation of maleimides with allenes has been disclosed, allowing the synthesis of optically active functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers in good to high yields along with good to high enantioselectivities.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc16904e