79644-02-3

Basic information

• Product Name: (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate
• Synonyms: (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate
• CAS NO: 79644-02-3
• Molecular Weight: 340.342
• Mol File: 79644-02-3.mol

Chemical Properties

• CAS DataBase Reference: (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate(79644-02-3)
• EPA Substance Registry System: (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate(79644-02-3)

Safety Data

• Hazardous Substances Data: 79644-02-3(Hazardous Substances Data)

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 6203-08-3 methyl 5-norbornene-2-carboxylate 
• 20445-31-2 R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 4835-96-5 (-)-menthyl acrylate 
• 67671-06-1 (2R)-endo-5-norbornene-2-methanol 
• 15507-06-9 5-norbornene-2-methanol 

Relevant articles and documents

221. Asymmetric Diels-Alder Reactions of Neopentyl-Ether-Shielded Acrylates and Allenic Esters: Syntheses of (-)-Norbornenone and (-)-β-Santalene

Starting from (+)- or (-)-camphor, the antipodal alcohols 14 and 18, respectively, have been prepared; the corresponding acrylates 15 and 19 underwent TiCl2(i-PrO)2-mediated Diels-Alder additions to cyclopentadiene to give adducts 20a and 22a respectively, with 95percent endo- and 99.2percent ?-face selectivities.Adduct 22a was converted to enentiomerically pure norbornenone 26.Addition of 1,3-butadiene to acrylate 15 in the presence of TiCl4 afforded 3-cyclohexenyl carboxylate 29 with > 95.6percent stereodifferentiation.The TiCl2(i-PrO)2-promoted cycloaddition of cyclopentadiene to allenic ester 43 proceeding with 99percent face differentiation served as the key step for an efficient enantioselective synthesis of (-)-β-santalene ((-)-41) with concomitant recovery of the chiral control alcohol 14.

A REINVESTIGATION OF ASYMMETRIC INDUCTION IN DIELS-ALDER REACTIONS

The chiral induction in the Diels-Alder addition 12, assessed reliably by (19)F-NMR-spectroscopy of the endo-esters 4, varied between 47-93 percent in favor of the 2-(R)-adducts 2 depending on the auxiliary chiral group and the Lewis-acid catalyst.