129568-84-9

Basic information

• Product Name: (2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam
• Synonyms: (2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam
• CAS NO: 129568-84-9
• Molecular Weight: 362.493
• Mol File: 129568-84-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam(129568-84-9)
• EPA Substance Registry System: (2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam(129568-84-9)

Safety Data

• Hazardous Substances Data: 129568-84-9(Hazardous Substances Data)

Upstream product

• 94594-90-8 (2R)-bornane-10,2-sultam 
• 645-45-4 hydrocinnamic acid chloride 
• 127392-81-8 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one 
• 654054-23-6 ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((2R,3R)-3-phenyl-aziridin-2-yl)-methanone 
• 129505-09-5 (2R,2'R)-N-<2'-(hydroxyamino)-3'-phenylpropanoyl>bornane-10,2-sultam 

Downstream Products

• 673-06-3 D-(R)-phenylalanine 

Relevant articles and documents

Asymmetric Synthesis of Arylalanines via Asymmetric aza-Darzens (ADZ) Reaction

(R)-3-Arylalanines may be prepared in high enantiomeric purity from N-dpp imines by a four-step reaction sequence involving asymmetric aza-Darzens reaction, dephosphinylation, hydrogenolysis and hydrolysis. The amino acids thus obtained were of >95% enantiomeric purity.

Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane

Successive treatment of N-acylsultams 3 with NaN(TMS)2, 1-chloro-1-nitrosocyclohexane (1) and 1N aq. HCl gave diastereomerically pure, crystalline N-hydroxyamino acid derivatives 4. Products 4 were converted to various amino acids 6, an N-BOC-amino acid 8 and to N-hydroxyamino acids 9. (S,S)-Isoleucine (16) was obtained from N-crotonoylsultam 13 via an organomagnesium-1,4-addition/enolate trapping process generating two stereogenic centers.