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2. Efficient Asymmetric Synthesis of (2R,3R)-3-{(1R)-1-[tert-Butyl(dimethyl)-siloxy]ethyl}-4-oxoazetidin-2-yl Acetate

Author

Fen-Er Chen, Jianping Huang, Hao Zhang, Zhong-Hua Wang, Shuang-Xi Gu, Lei Zhao, and Hui-Fang Dai

Subjects
chemistry.chemical_classification, Aldimine, Ketone, Stereochemistry, Organic Chemistry, Imine, Enantioselective synthesis, Ascorbic acid, Medicinal chemistry, Catalysis, chemistry.chemical_compound, chemistry, Titanium tetrachloride, Mitsunobu reaction, Diketene
Abstract

R,3R)-3-{(1R)-1-(tert-Butyl(dimethyl)siloxy)ethyl}- 4-oxoazetidin-2-yl acetate was efficiently prepared from L-ascorbic acid. The key steps were the a highly diastereoselective (2 + 2) cy- cloaddition of diketene with an (S)-glyceraldehyde-derived ald- imine to give the ketone, stereoselective titanium tetrachloride mediated asymmetric reduction to give the corrsponding S-config- ured alcohol, and Mitsunobu inversion of the latter to give the de- sired R-configured alcohol.

Published
2011
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3. Efficient Asymmetric Synthesis of (2R,3R)-3-((1R)-1-[tert-Butyl(dimethyl)- siloxy]ethyl)-4-oxoazetidin-2-yl Acetate.

Author

Jian-Ping Huang, Lei Zhao, Shuang-Xi Gu, Zhong-Hua Wang, Hao Zhang, Fen-Er Chen, and Hui-Fang Dai

Subjects
CARBAPENEMS, HETEROCYCLIC compounds, RING formation (Chemistry), VITAMIN C, KETONES, TITANIUM tetrachloride
Abstract

(2R,3R)-3-((1R)-1-[tert-Butyl(dimethyl)siloxy]ethyl)- 4-oxoazetidin-2-yl acetate was efficiently prepared from L-ascorbic acid. The key steps were the a highly diastereoselective [2 + 2] cycloaddition of diketene with an (S)-glyceraldehyde-derived aldimine to give the ketone, stereoselective titanium tetrachloride mediated asymmetric reduction to give the corrsponding S-configured alcohol, and Mitsunobu inversion of the latter to give the desired R-configured alcohol. [ABSTRACT FROM AUTHOR]

Published
2011
Full Text
View/download PDF

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