188115-58-4

Upstream product

• 53250-10-5 2-(2-methylallyloxy)tetrahydro-2H-pyran 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 39924-63-5 (Z)-3-phenyl-2-methyl-2-propenol 
• 1504-55-8 (E)-3-phenyl-2-methyl-2-propenol 
• 188115-61-9 Propionic acid (E)-2-methyl-3-phenyl-allyl ester 
• 103305-34-6 anti-ethyl 2,4-dimethyl-3-phenyl-4-pentenoate 
• 103305-34-6 syn-ethyl 2,4-dimethyl-3-phenyl-4-pentenoate 
• 103305-38-0 (2R,3R)-4-Methyl-3-phenyl-2-propyl-pent-4-enoic acid methyl ester 
• 103305-38-0 (2S,3R)-4-Methyl-3-phenyl-2-propyl-pent-4-enoic acid methyl ester 
• 103305-36-8 (2R,3R)-2-Ethyl-4-methyl-3-phenyl-pent-4-enoic acid methyl ester 
• 103305-36-8 (2S,3R)-2-Ethyl-4-methyl-3-phenyl-pent-4-enoic acid methyl ester 

Relevant academic research and scientific papers

Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement

The ortho ester Claisen rearrangement of trisubstituted allylic alcohols exhibits significant levels of diastereoselection. In E allylic alcohols, a 1,3-diaxial interaction develops in the chairlike transition state leading to the anti isomer, rendering the reaction syn selective by a factor of 3-5 to 1. In Z allylic alcohols, the 1,3-diaxial interaction develops in the transition state leading to the syn isomer, generating an anti:syn selectivity of 6-15 to 1. The relative stereochemistry of the syn isomer was confirmed independently by the synthesis of the mycotoxin botryodiplodin.