116706-45-7

Upstream product

• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 852635-75-7 CH₃CHCHCHAl(CH₂CH(CH₃)2)2OCON(CH(CH₃)2)2 
• 333722-11-5 4,4,5,5-tetramethyl-2-{(E)-1-[methyl(methylsulfonyl)amino]-2-butenyl}-1,3,2-dioxaborolane 
• 118573-97-0 (1R*,2R*)-(Z)-4-methoxy-2-methyl-1-phenyl-3-buten-1-ol 

Relevant academic research and scientific papers

(E)-α-Sulfonamidocrotylboronates as reagents for the stereoselective homoaldol synthesis

The α-sulfonamidocrotylboronates 9 and 10 have been generated by nucleophilic substitution at the α-chlorocrotylboronates 1b, in yields of up to 70%. The α-sulfonamidocrotylboronates 9 and 10 react with aldehydes at room temp. and 4 kbar pressure to give the anti-homoallylic alcohols 13 and 14 with high simple diastereoselectivity. These latter may be directly converted into the lactol ethers 15 in a one-pot procedure.

Stereoselective Synthesis of Alcohols, XXIX. - Addition of (α-Methoxycrotyl)boronates to Aldehydes

α-Phenoxy- (4) and α-methoxycrotylboronates (8) were obtained from the α-chlorocrotylboronates 1.Addition of the phenoxy compound to aldehydes gave the homoallyl alcohols 5/6 as Z/E mixtures; addition of the methoxy compound led to essentially pure Z-enol ethers 9.Enantiomerically enriched (ca. 90percent e.e.) 8 was used in reactions with chiral aldehydes to ensure the formation of the new stereogenic centers under reagent control of diastereoselectivity. - Key Words: Reagent control of stereoselectivity / Z-Enol ether, formation of / Allylboronates, addition to aldehydes