1365547-75-6

Basic information

• Product Name: (S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine
• Synonyms: (S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine
• CAS NO: 1365547-75-6
• Molecular Weight: 243.757
• Mol File: 1365547-75-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine(CAS DataBase Reference)
• NIST Chemistry Reference: (S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine(1365547-75-6)
• EPA Substance Registry System: (S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine(1365547-75-6)

Safety Data

• Hazardous Substances Data: 1365547-75-6(Hazardous Substances Data)

Upstream product

• 917-93-1 2-chloroisobutyraldehyde 
• 188447-91-8 (S)-p-toluenesulfinimide 

Downstream Products

• 1365547-86-9 (S(S),2S,2'R)-ethyl 2-(diphenylmethylamino)-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetate 
• 1365548-16-8 (S(S),2R,3R)-ethyl 2-amino-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1365548-30-6 (S(S),2S,2'R)-ethyl 2-(diphenylmethyleneamino)-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetate 
• 1365548-24-8 (S(S),2R,2'R)-ethyl 2-(diphenylmethyleneamino)-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetate 
• 1365548-17-9 (S(S),2R,3R)-ethyl 2-(diphenylmethyleneamino)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1365548-18-0 (S(S),2S,3R)-ethyl 2-(diphenylmethyleneamino)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1365548-34-0 (S(S),2R,3R)-tert-butyl 2-(diphenylmethyleneamino)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1365548-22-6 (S(S),2S,3R)-tert-butyl 2-(diphenylmethyleneamino)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1365548-20-4 (S(S),2R,3R)-methyl 2-(diphenylmethyleneamino)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1365548-29-3 (S(S),2R,2'R)-methyl 2-(diphenylmethyleneamino)-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetate 
• 1609490-94-9 (S_s,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1609490-93-8 (S_s,2S,3S)-methyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1609490-92-7 (S_s,2S,3S)-benzyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1425458-23-6 (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine 

Relevant articles and documents

Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines

The efficient asymmetric synthesis of new chiral γ-chloro-α, β-diamino acid derivatives via highly diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral α-chloro-N-p-toluenesulfinylimine was developed. The influence of the base, LDA or LiHMDS, used for the formation of the glycine enolates, was of great importance for the anti-/syn-diastereoselectivity of the Mannich-type reaction. The γ-chloro-α,β-diamino acid derivatives proved to be excellent building blocks for ring closure towards optically pure anti- and syn-β,γ-aziridino-α-amino esters, and subsequent ring transformation into trans-3-aminoazetidine-2-carboxylic acid derivatives and α,β-diamino-γ-butyrolactones. The Royal Society of Chemistry 2012.