137151-87-2

Upstream product

• 129520-87-2 (S)-3-phenyl-1-(trimethylsilyl)-4-penten-1-one 
• 80816-24-6 (E)-[3-(vinyloxy)prop-1-en-1-yl]benzene 
• 29526-96-3 1-phenylcyclopropan-1-ol 
• 93-89-0 benzoic acid ethyl ester 
• 4510-34-3 (Z)-cinnamyl alcohol 

Downstream Products

• 1154743-87-9 (S)-3-phenylpent-4-en-1-ol 

Relevant academic research and scientific papers

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.

Enantioselective activation of ethers by chiral organoaluminum reagents: Application to asymmetric Claisen rearrangement

The asymmetric Claisen rearrangement of allyl vinyl ethers has been effected with a chiral organoaluminum reagent, (R)-1 or (S)-1 as an example of the enantioselectie activation of ether substrates. This method provides a facile asymmetric synthesis of various acylsilanes and acylgermanes with high optical purity. Among various trialkylsilyl substituents of chiral organoaluminum reagent 1, use of the more bulky t-butyldiphenylsilyl group exhibits the highest enantioselectivity. The conformational analysis of two possible chairlike transition-state structures of an allyl vinyl ether substrate reveals that a chiral organoaluminum reagent 1 can discriminate between these two conformations only by a difference in the orientation of α-methylene groups of ethers.