Asymmetric Synthesis of α‐Amino Acids Bearing a 3‐Alkyloxindole Structural Motif. Issue 47 (14th December 2021)

• Record Type: Journal Article
• Authors: Wang, Xiao‐Ping; Liu, Yong‐Liang; Wei, Jie; Chen, Ling‐Yan; Li, Ya
• Is Part Of: ChemistrySelect. Volume 6:Issue 47(2021)
• Page Start: 13499
• Page End: 13505
• Publication Date: 2021-12-14
• Subjects: amines -- amino acids -- chirality -- diastereoselectivity -- nucleophilic addition; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202102857
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: We report a diastereoselective Mannich‐type reaction of 3‐alkyloxindole with N‐ tert ‐butanesulfinyl imino ester. This method provides a concise route to α‐amino acid derivatives bearing a 3‐alkyloxindole structural motif. This protocol has the advantage of using readily accessible starting materials and is operationally simple. A plausible transition‐state mode for the observed stereoselectivity is presented. Abstract : A diastereoselective Mannich‐type reaction of 3‐alkyloxindole with N‐ tert ‐butanesulfinyl imino ester is developed, which provides a concise route to α‐amino acid derivatives bearing a 3‐alkyloxindole structural motif. This protocol has the advantage of using readily accessible starting materials and is operationally simple. A chair‐like transition‐state mode for the observed stereoselectivity is proposed.