143077-25-2

Basic information

• Product Name: (1S,5S,7S)-7-Benzooxazol-2-yl-1,5,7-trimethyl-3-(2-methylene-cyclopentanecarbonyl)-3-aza-bicyclo[3.3.1]nonan-2-one
• CAS NO: 143077-25-2
• Molecular Weight: 406.525
• Mol File: 143077-25-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,5S,7S)-7-Benzooxazol-2-yl-1,5,7-trimethyl-3-(2-methylene-cyclopentanecarbonyl)-3-aza-bicyclo[3.3.1]nonan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5S,7S)-7-Benzooxazol-2-yl-1,5,7-trimethyl-3-(2-methylene-cyclopentanecarbonyl)-3-aza-bicyclo[3.3.1]nonan-2-one(143077-25-2)
• EPA Substance Registry System: (1S,5S,7S)-7-Benzooxazol-2-yl-1,5,7-trimethyl-3-(2-methylene-cyclopentanecarbonyl)-3-aza-bicyclo[3.3.1]nonan-2-one(143077-25-2)

Safety Data

• Hazardous Substances Data: 143077-25-2(Hazardous Substances Data)

Upstream product

• 43001-25-8 4-iodobut-1-yne 
• 143077-24-1 (R)-(-)-<1α,3(E),5α,7β>-4-<7-(2-benzoxazolyl)-1,5,7-trimethyl-2-oxo-3-azabicyclo<3.3.1>non-3-yl>-4-oxo-2-propenoic acid 

Relevant articles and documents

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.