Diastereoselective Synthesis of 尾-Heteroaryl syn-伪-Methyl-尾-Amino Acid Derivatives via a Double Chiral Auxiliary Approach

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• 作者：Jianwei Bian ; David Blakemore ; Joseph S. Warmus ; Jianmin Sun ; Matthew Corbett ; Colin R. Rose ; Bruce M. Bechle
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：February 1, 2013
• 年：2013
• 卷：15
• 期：3
• 页码：562-565
• 全文大小：329K
• 年卷期：v.15,no.3(February 1, 2013)
• ISSN：1523-7052

文摘

The addition of the SuperQuat enolate to five- and six-membered heterocyclic tert-butyl sulfinimines led to a high syn-selectivity of up to 99:1 in good to excellent yields. The reaction is tentatively proposed to proceed through an open-chain transition state with the presence of an 伪-heteroatom on the sulfinimine leading to high diastereoselectivities. The adducts were derivatized to 尾-amino esters and amides in a facile manner.