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A concise construction of carbohydrate-tethered axially chiral allenes via copper catalysis
Literature Information
Publication Date
2015-06-16
DOI
10.1039/C5QO00164A
Impact Factor
5.281
Authors
Xin Huang, Can Xue, Chunling Fu, Shengming Ma
View Original
Abstract
The efficient construction of the axial chirality of allenes bearing a carbohydrate unit is challenging. Here we observed that the newly developed CuBr2 catalysis may smoothly catalyze the highly diastereoselective three-component reaction of carbohydrates bearing a terminal alkyne unit, aliphatic or aromatic aldehydes, and (R) or (S)-α,α-diphenylprolinol, affording carbohydrates bearing the chiral 1,3-substituted allene entity in very high de (94–99%). Synthetically attractive functionalities, such as hydroxyl, amide, malonate, and even tosylate, etc. could all be well tolerated. The role of the carbohydrate unit has been explored.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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