Journal
ORGANIC LETTERS
Volume 15, Issue 10, Pages 2422-2425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400898p
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Funding
- Japan Society for the Promotion of Science (JSPS) [24350022]
- Adaptable and Seamless Technology Transfer Program through Target-driven RAMP
- D from the Japan Science and Technology Agency (JST) [AS242Z02711Q]
- Grants-in-Aid for Scientific Research [25620028, 24750037] Funding Source: KAKEN
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An asymmetric Strecker-type reaction of nitrones using acetone cyanohydrin as a source of HCN has been realized. A magnesium-tartramide complex, generated from (R,R)-2,3-dihydroxy-1,4-di(pyrrolidin-1-yl)-butane-1,4-dione and MeMgBr, promoted transcyanation from the bromomagnesium salt of the cyanohydrin, in the presence of a catalytic amount of DBU, to afford the corresponding optically active (S)-alpha-amino nitrile derivatives. The reaction was applicable to various nitrones giving high-to-excellent enantioselectivities.
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