79298-54-7

Upstream product

• 60656-87-3 benzyloxyacetoaldehyde 
• 804559-38-4 (R,R)-crotylsilane 
• 804559-39-5 (R,R)-trans EZ-CrotylMix 
• 1280227-87-3 (2S,3S,E)-1-(benzyloxy)-3-methyl-5-(tributylstannyl)pent-4-en-2-ol 
• 61209-24-3 (Z)-3-methyl-2-butenyltrichlorosilane 
• 18147-55-2 (Z)-crotyltrichlorosilane 

Relevant academic research and scientific papers

Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide

We have demonstrated that bidentate Lewis base catalysts can be constructed based on the Cinchona alkaloid structure that promote highly stereoselective reactions of allyl- and crotyltrichlorosilane with aromatic as well as aliphatic aldehydes (90-99% ee, >98% diastereoselectivity). The catalysts are available in a one-pot procedure in >70% yield from cheap starting materials and promote the allylation reactions at ambient temperature. Gram scale reactions with catalyst recovery and reuse showcased the practicality of the catalytic system.

A new and more powerfully activating diamine for practical and scalable enantioselective aldehyde crotylsilylation reactions

A new diaminophenol ligand for crotylsilylation reactions with cis- and trans-crotyltrichlorosilane has been developed. The conformational constraints that result from the tethering of the phenol to one of the amino groups attenuate the stereoelectronic effects that reduce activity in the corresponding untethered diaminosilanes, and the resulting crotylsilane reagents are as active as our previously reported EZ-CrotylMix reagents, but without requiring the use of the Sc(OTf)3 catalyst. In turn, this has allowed the development of an experimentally straightforward, sustainable, efficient, and scalable one-pot procedure which may be carried out in ≤8 hours, and in which the diaminophenol activator ligand may be easily recovered in ≥90% yield by recrystallization.

Enantioconvergent hydroboration of a racemic allene: Enantioselective synthesis of (E)-δ-stannyl- anti -homoallylic alcohols via aldehyde crotylboration

The enantioconvergent hydroboration of racemic allenylstannane (±)-1 with (dIpc)2BH converts both enantiomers of (±)-1 into the enantioenriched crotylborane (S)-E-3. Subsequent crotylboration of aldehydes with (S)-E-3 provides (E)-st

A more comprehensive and highly practical solution to enantioselective aldehyde crotylation

The enantioselective crotylation of aldehydes with 1,2- diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf) 3. The one significant limitation on the utility of these reagents-substrate scope-has thus been addressed. The net r

Highly diastereo- and enantioselective reagents for aldehyde crotylation

(Chemical Equation Presented) Two new, crystalline solid, storable, and highly enantioselective reagents for aldehyde crotylation have been developed. Both (cis and trans) crotylsilane reagents are easily prepared in bulk, require trivial reaction conditi