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Reaction of Silyllithium, alpha-Keto N-tert-Butanesulfinyl Imidates and Aldehydes for Asymmetric Synthesis of alpha-Substituted beta-(Silyloxy)-alpha-hydroxy Acid Derivatives
Huang, W (Huang, Wei); Liu, H (Liu, Hui); Xu, YJ (Xu, Yan-Jun); Lu, CD (Lu, Chong-Dao); Lu, CD
2017
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
Volume82Issue:19Pages:10748-10755
Abstract

A single-flask reaction of silyllithium, a-keto alpha-tert-butanesulfinyl imidates and aldehydes has been developed for the diastereoselective synthesis of alpha,beta-dihydroxy acid derivatives. In this reaction, the nucleophilic addition of silyllithium to chiral a-keto imidates followed by silyl migration forms chiral aza-enolates, which react diastereoselectively with aldehydes. Subsequent [1,4]-O -> O silyl migration affords a-substituted beta-(silyoxy)-alpha-hydroxy imidates.

DOI10.1021/acs.joc.7b02214
Indexed BySCI
WOS IDWOS:000412789000087
Citation statistics
Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5277
Collection省部共建新疆特有药用资源利用重点实验室
Corresponding AuthorLu, CD
Affiliation1.Chinese Acad Sci, Key Lab Plant Resources & Chem Arid Zones, Xinjiang Tech Inst Phys & Chem, Urumqi 830011, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Huang, W ,Liu, H ,Xu, YJ ,et al. Reaction of Silyllithium, alpha-Keto N-tert-Butanesulfinyl Imidates and Aldehydes for Asymmetric Synthesis of alpha-Substituted beta-(Silyloxy)-alpha-hydroxy Acid Derivatives[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(19):10748-10755.
APA Huang, W ,Liu, H ,Xu, YJ ,Lu, CD ,&Lu, CD.(2017).Reaction of Silyllithium, alpha-Keto N-tert-Butanesulfinyl Imidates and Aldehydes for Asymmetric Synthesis of alpha-Substituted beta-(Silyloxy)-alpha-hydroxy Acid Derivatives.JOURNAL OF ORGANIC CHEMISTRY,82(19),10748-10755.
MLA Huang, W ,et al."Reaction of Silyllithium, alpha-Keto N-tert-Butanesulfinyl Imidates and Aldehydes for Asymmetric Synthesis of alpha-Substituted beta-(Silyloxy)-alpha-hydroxy Acid Derivatives".JOURNAL OF ORGANIC CHEMISTRY 82.19(2017):10748-10755.
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