129505-11-9

Upstream product

• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 108448-77-7 (+)-camphorsultam 
• 129505-04-0 (2S)-N-<(4-methoxyphenyl)acetyl>bornane-10,2-sultam 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 129505-04-0 (2R)-N-<(4-methoxyphenyl)acetyl>bornane-10,2-sultam 

Downstream Products

• 24593-48-4 (2S)-2-amino-2-(4-methoxyphenyl)acetic acid 
• 24593-49-5 D-(-)-2-(4-methoxyphenyl)glycine 
• 129505-13-1 (2S,2'S)-N-<2'-amino-2'-(4''-methoxyphenyl)acetyl>bornane-10,2-sultam hydrochloride 
• 129505-13-1 (2R,2'R)-N-<2'-amino-2'-(4''-methoxyphenyl)acetyl>bornane-10,2-sultam hydrochloride 

Relevant academic research and scientific papers

Asymmetric Synthesis of α-Amino Acids and α-N-Hydroxyamino Acids from N-Acylbornane-10,2-sultams: 1-Chloro-1-nitrosocyclohexane as a Practical +> Equivalent

Successive treatment of N-acylsultams 3 with sodium hexamethyldisilazide, 1-chloro-1-nitrosocyclohexane (1), and aq.HCl gave diastereoisomerically pure, crystalline N-hydroxyamino-acid derivatives 5.These were converted into various amino acids 7, N-hydroxyamino acids 8, and an N-Boc-amino acid 9. (S,S)-Isoleucine (17) and (S,S)-2-acetamido-3-phenylbutyric acid (23) were obtained from N-crotonoylsultam 15 via 1,4-addition of an organomagnesium or organocopper reagent followed by enolate 'amination' with 1.

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.