188308-53-4

Upstream product

• 6253-27-6 4,5-epoxy-cyclohexene 
• 183065-61-4 ((1S,3R,4R,6R)-4-Azido-7-oxa-bicyclo[4.1.0]hept-3-yloxy)-triisopropyl-silane 
• 188308-51-2 ((1R,6R)-6-Azido-cyclohex-3-enyloxy)-trimethyl-silane 
• 188308-52-3 (1R,2R,4R,5R)-5-Azido-2-phenylselanyl-4-triisopropylsilanyloxy-cyclohexanol 

Downstream Products

• 167937-56-6 N-[(3R,4R)-hexahydro-4-hydroxy-1-(phenylmethyl)-1H-azepin-3-yl]-4-(phenylmethoxy)benzamide 
• 183065-59-0 (3R,4R)-3-Azido-1-benzyl-4-triisopropylsilanyloxy-2,3,4,7-tetrahydro-1H-azepine 
• 188308-56-7 (5R,6R)-6-Azido-1-benzyl-5-triisopropylsilanyloxy-1,5,6,7-tetrahydro-azepin-2-one 
• 188308-57-8 4-Benzyloxy-N-((3R,4R)-1-benzyl-4-triisopropylsilanyloxy-azepan-3-yl)-benzamide 
• 183065-62-5 (4R,5R)-5-Azido-4-triisopropylsilanyloxy-cyclohex-2-enone 

Relevant academic research and scientific papers

An efficient formal synthesis of balanol via the asymmetric epoxide ring opening reaction

An efficient formal synthesis of balanol is described. The thirteen-step sequence features a highly enantioselective (92% ee) ring opening of 1,4-cyclohexadiene monoepoxide with TMSN3 catalyzed by the Cr-salen complex 3. A selective Beckmann rearrangement followed by amide reduction and nitrogen functionalization affords 2, thus completing a formal synthesis of balanol in 31% overall yield.