1203546-60-4

Basic information

• Product Name: (S)-ethyl 3,3-dimethyl-2-[(S)-phenylmethanesulfinamido]butanoate
• Synonyms: (S)-ethyl 3,3-dimethyl-2-[(S)-phenylmethanesulfinamido]butanoate
• CAS NO: 1203546-60-4
• Molecular Weight: 297.419
• Mol File: 1203546-60-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-ethyl 3,3-dimethyl-2-[(S)-phenylmethanesulfinamido]butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-ethyl 3,3-dimethyl-2-[(S)-phenylmethanesulfinamido]butanoate(1203546-60-4)
• EPA Substance Registry System: (S)-ethyl 3,3-dimethyl-2-[(S)-phenylmethanesulfinamido]butanoate(1203546-60-4)

Safety Data

• Hazardous Substances Data: 1203546-60-4(Hazardous Substances Data)

Upstream product

• 62673-31-8 benzyl(bromo)zinc 

Downstream Products

• 62965-35-9 N-tert-butyloxycarbonyl-L-tert-leucine 
• 69557-34-2 ethyl (S)-2-amino-3,3-dimethylbutanoate 

Relevant articles and documents

Radical migration-addition of N-tert-butanesulfinyl imines with organozinc reagents

A novel migration-addition sequence was discovered for the reaction of enantioenriched N-tert-butanesulfinyl iminoacetate 1a with functionalized benzylzinc bromide reagents, producing tert-leucine derivatives in excellent diastereoselectivity (dr 98:2). The absolute configurations of two new chiral centers were unambiguously assigned by chemical transformations and X-ray crystallography. In addition, the regio- and diastereoselectivities of this novel reaction were both explained through the key N-sulfinamine intermediate M6 generated by the tert-butyl radical attack on the imine. Computational analysis of this reaction process, which was performed at the B3LYP/6-311++G(3df,2p)//B3LYP/6-31G-LANL2DZ level, also supported our proposed two-stage mechanism.