147973-86-2Relevant academic research and scientific papers
Applications of remote stereocontrol using allylstannanes: An approach to the stereoselective synthesis of aliphatic polyols
McNeill, Alan H.,Thomas, Eric J.
experimental part, p. 257 - 266 (2011/02/27)
(4R,2E)-4-Benzyloxy-octa-2,7-dienyl(tributyl)stannane was transmetalated by tin(IV) chloride to generate an allyltin trichloride, which reacted with aldehydes to give (3Z)-1,5-syn-5-benzyloxynona-3,8-dien-1-ols with useful 1,5-stereocontrol. O-Benzylation, hydroboration and oxidation of the terminal double-bond of the product from 2-methylpropanal gave (5R,9S,6Z)-5,9- dibenzyloxy-10-methylundec-6-enal. Further reactions with 4-alkoxyalk-2- enylstannanes proceeded with useful 1,5-stereocontrol to give open-chain products with hydroxy or benzyloxy substituents stereoselectively disposed at remote positions along the chain.
Stereoselective Synthesis of Aliphatic 1,5,9,13-Polyols using (δ-Alkoxyallyl)stannanes
McNeill, Alan H.,Thomas, Eric J.
, p. 1669 - 1672 (2007/10/02)
Treatment of aliphatic aldehydes with the allyltin trichloride generated from the 4-benzyloxyocta-2,7-dienylstannane 18 and tin(IV)chloride provides stereoselective access to polyhydroxylated compounds with the hydroxyl groups at positions 1,5,9,13- etc.
