116706-41-3Relevant academic research and scientific papers
CHIRAL α-METHOXY-E-CROTYLBORONATES, REAGENTS FOR STEREOSELECTIVE C-C-BOND FORMATION UNDER REAGENT CONTROL OF DIASTEREOSELECTIVITY
Hoffmann, Reinhard W.,Dresely, Stefan
, p. 5303 - 5306 (1987)
Treatment of the previously described α-chloro-E-crotylboronate with lithium-methoxide in THF furnished the title compound 6 of 88-94 percent e.e.On addition to achiral aldehydes complete transfer of chirality was realized, resulting in the β-methyl-homoallyl alcohols 7 with a Z-configuration of the enol-ether double bond.On reaction of 6 with chiral aldehydes excellent (matched pair) to good (mismatched pair) selectivities in favor of the stereotriades C or D respectively were realized.
ALLYLIC 1,3-REARRANGEMENT OF 1-ALKOXYALLYLPHOSPHONIUM SALTS. REGIOCHEMISTRY OF REACTION OF 1-ALKOXY-2-ALKENYLENEPHOSPHORANES WITH ALDEHYDES
Kim, Sunggak,Kim, Youn Chul
, p. 2901 - 2904 (2007/10/02)
It was found that 1-alkoxyallylphosphonium salts underwent allylic 1,3-rearrangement to afford 3-alkoxyallylphosphonium salts.Reaction of 1-alkoxy-2-alkenylene-phosphoranes with aldehydes gave α-adducts, whereas the reaction in the presence of TMSOTf gave γ-adducts.
Stereoselective Synthesis of Alcohols, XXIX. - Addition of (α-Methoxycrotyl)boronates to Aldehydes
Hoffmann, Reinhard W.,Dresely, Stefan
, p. 903 - 910 (2007/10/02)
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
