104283-96-7Relevant academic research and scientific papers
Hydrated ?-bonded organometallic cations in organic synthesis. I. Allyl-, crotyl-, 1-methylallyl-, cyclohex-2-enyl-, and cinnamyl-stannation of carbonyl compounds in water
Furlani, Donatella,Marton, Daniele,Tagliavini, Giuseppe,Zordan, Michele
, p. 345 - 356 (1988)
Homoallylic alcohols can be prepared in water by allyl-, crotyl-, 1-methylallyl-, cyclohex-2-enyl-, or cinnamyl-stannation of such carbonyl compounds as aldehydes, dialdehydes, and ketones, as well as acetals.The procedure is based on: Bu2RSnCl + R'COR" + (1/2)H2O -> R(HO)CR'R" + (1/2)(Bu2SnCl)2O where R = allyl, crotyl, 1-methylallyl, cyclohex-2-enyl, or cinnamyl group, R' = H or alkyl group, R" R'= alkyl group.In most cases, the reaction products are obtained rapidly in high yields (80-100percent).Hydrated organometallic cations Bu2RSn+(aq) are partly involved.These results, together with those already published on 2-propynyl-and allenyl-stannation, indicate the value of this procedure.
Aldehyde addition to allylic stannanes via a transmetallation pathway: Stereocontrol in the absence of internal coordination
Marshall, Raymond L.,Muderawan, I. Wayan,Young, David J.
, p. 957 - 962 (2007/10/03)
Methyltin trichloride and indium(III) chloride promote the addition of aldehydes to cyclic allylic stannanes providing good yields of the corresponding homoallylic alcohols. These reactions proceed via an initial transmetallation involving anti approach of the electrophile, followed by syn aldehyde addition that is erythro selective. These Lewis acids do not promote the corresponding addition of imines, rather providing the same homoallylic alcohols after an in situ aqueous hydrolysis. Imine addition is possible with boron trifluoride-diethyl ether as the Lewis acid.
Stereochemical Aspects of Aldehyde Additions to Cyclohex-2-enylstannanes
Young, David,Kitching, William
, p. 1767 - 1777 (2007/10/02)
Cyclohex-2-enylation of aldehydes, mediated with boron trifluoride etherate, involves γ-equatorial approach of the presumed aldehyde-Lewis acid adduct (RCHO-BF3), irrespective of starting stannane stereochemistry.Marginal threo selectivity characterizes homoallyl alcohol formation from benzaldehyde, whereas alkanals react with high erythro selectivity, so that 1-(1'-hydroxyalkyl)cyclohex-2-enes in this diastereomeric form are available based on allyltin chemistry.
