422570-19-2

Basic information

• Product Name: (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one
• Synonyms: (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one
• CAS NO: 422570-19-2
• Molecular Weight: 297.397
• Mol File: 422570-19-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one(422570-19-2)
• EPA Substance Registry System: (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one(422570-19-2)

Safety Data

• Hazardous Substances Data: 422570-19-2(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 422570-15-8 (1R,2S,8S)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one 
• 100-44-7 benzyl chloride 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 10334-26-6 (R)-camphorquinone 
• 422570-14-7 (1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester 
• 23963-14-6 (1S,4R)-4,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxolan]-3-one 
• 23963-16-8 (1S,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one 

Downstream Products

• 898823-55-7 (1R,2S,5S,8S)-5-benzyl-1,5,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one 
• 105743-57-5 (S)-2-amino-2-benzyl-4-pentenoic acid 
• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 
• 898823-56-8 (1R,2S,5S,8S)-5-allyl-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one 
• 673-06-3 D-(R)-phenylalanine 

Relevant articles and documents

Temperature-Dependent Enantio- and Diastereodivergent Synthesis of Amino Acids with One or Multiple Chiral Centers

A general and facile methodology for temperature-dependent enantiodivergent and diastereodivergent synthesis of amino acids with one or multiple chiral centers was developed. Camphor-based tricyclic iminolactones attack electrophiles from the endo face at low temperature (-78 to -40 °C) and from the exo face at high temperature (-10 to 25 °C).

Chiral tricyclic iminolactone derived from (1R)-(+)-camphor as a glycine equivalent for the asymmetric synthesis of α-amino acids

The development of a highly efficient and stereoselective methodology for the preparation of α-amino acids is described. The chiral template, tricyclic iminolactone 7, was synthesized from (1R)-(+)-camphor in five steps in 50% overall yield. Alkylation of iminolactone 7 afforded the α-monosubstituted products in good yields (74-96%) and excellent diastereoselectivities (>98%). Hydrolysis of the alkylated iminolactones furnished the desired α-amino acids in good yields and enantioselectivities with nearly quantitative recovery of the chiral auxiliary 4.