51795-28-9

Upstream product

• 143143-12-8 (4R,1'R,2'R)-4-(2'-trifluoroacetamido-1'-phenylpropoxy)hex-1-ene 

Downstream Products

• 252191-20-1 (3R,4R,5S)-4-Acetylamino-5-azido-3-((R)-1-ethyl-but-3-enyloxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 252191-23-4 (3R,4R,5S)-4-Acetylamino-5-azido-3-((R)-1-ethyl-3-oxo-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 252191-18-7 (3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-ethyl-3-hydroxy-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 252191-21-2 (3R,4R,5S)-4-Acetylamino-5-azido-3-((R)-1-oxiranylmethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 252191-17-6 (3R,4R,5S)-4-Acetylamino-5-amino-3-((R)-1-carboxymethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 252191-22-3 (3R,4R,5S)-4-Acetylamino-5-azido-3-((R)-1-ethyl-3,4-dihydroxy-butoxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 1036926-72-3 (R)-[(hex-5-en-3-yloxy)methyl]benzene 

Relevant academic research and scientific papers

Synthesis of Enantiopure Homoallylic Alcohols and Ethers by Diastereoselective Allylation of Aldehydes

Enantiopure homoallylic alcohols 5, which are important building blocks in organic synthesis, are obtained with an ee of greater than 99percent and a yield of 75-95percent by cleavage of the secondary homoallylic ethers 4 using sodium in liquid ammonia.The ethers 4 are formed with excellent diastereoselectivity and in 52-89percent yield by treatment of the aldehydes 1 with the trimethylsilyl ether of N-trifluoroacetylnorpseudoephedrine (2) in the presence of a catalytic amount of TMS triflate or TMS borontriflate, followed by addition of allylsilane 3.Nearly all achiral aliphatic aldehydes employed gave a diastereoselectivity of over 99:1.With the chiral aldehydes 24, the difference between matched and mismatched pairs was low; this reveals that there is strong reagent control.- Keywords: allylations; allylsilanes; double stereodifferentiation; ephedrine; homoallylic alcohols