848360-10-1

Upstream product

• 112571-33-2 (1S,2S)-1-phenyl-2-methoxy-3-buten-1-ol 
• 100-52-7 benzaldehyde 
• 77896-96-9 2-<(Z)-3-methoxy-2-propenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 848359-88-6 (1R,2S)-1-tert-butyldimethylsilyloxy-2-methoxy-1-phenylbut-3-ene 
• 848359-89-7 (1R,2S)-2-methoxy-1-phenyl-1-(triisopropylsilyloxy)but-3-ene 

Relevant academic research and scientific papers

Diastereoselective synthesis of unsaturated 1,2-amino alcohols from α-hydroxy allyl ethers using chlorosulfonyl isocyanate

Diastereoselective synthesis of 1,2-amino alcohols was achieved from a highly diastereoselective allylic amination reaction of α-hydroxy allyl ethers using chlorosulfonyl isocyanate. Diastereoselectivities varied depending on the stereochemistry of the ethers used and the stability of the carbocation intermediate obtained during the reaction. We propose that this CSI reaction is the results of either a SNi or SN1 mechanism, according to the stability of the carbocation intermediate.

LIMITED DIASTEREOSELECTIVITY ON ADDITION OF γ-ALKOXY-Z-ALLYLBORONATES TO ALDEHYDES

Addition of Z-γ-alkoxy-allylboronates 2 to aldehydes leads to the homoallylalcohls 3 and 4.Increased steric bulk both on the aldehyde part or the allylboronates causes a decrease in diastereoselectivity.The stereochemistry of the addition is established by novel synthesis of exo-brevicomine.