143077-07-0

Upstream product

• 135311-52-3 endo-N-(2-hydroxyphenyl)-1,5,7-trimethyl-2,4-dioxo-3-azabicyclo<3.3.1>nonane-7-carboxamide 
• 118514-36-6 (1S,5R,7R)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid 
• 118514-37-7 (1S,5R,7R)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride 
• 79410-20-1 Kemp's triacid 

Downstream Products

• 143077-08-1 (1S,5R,7S)-1,5,7-Trimethyl-2-oxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (2-hydroxy-phenyl)-amide 
• 135311-54-5 (1S,5S,7S)-7-Benzooxazol-2-yl-1,5,7-trimethyl-2-oxo-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 135311-54-5 (1R,5R,7R)-7-Benzooxazol-2-yl-1,5,7-trimethyl-2-oxo-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 135311-58-9 <1R-<1α,3(SR),5α,7β>>-7-(2-benzoxazolyl)-α-cyclohexyl-1,5,7-trimethyl-γ,2-dioxo-3-azabicyclo<3.3.1>nonane-3-butanoic acid, ethyl ester 

Relevant academic research and scientific papers

A new chiral auxiliary for asymmetric thermal reactions: High stereocontrol in addition, allylation, and annulation reactions

A new imide chiral auxiliary, endo-7-(2-benzoxazolyl)-1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one (5), is prepared from Kemp's triacid and resolved via its menthyl carbamate. Mixed fumarate derivatives of the auxiliary show unprecedented control of regiochemistry and β-stereochemistry in representative radical addition reactions. Chiral radicals derived from 5 also show extremely high levels of stereoselectivity in representative radical allylation and cyclization reactions. Structural features of the chiral auxiliary and features of radical addition are integrated into a model for stereoselection.