88015-29-6Relevant academic research and scientific papers
Remote Nucleophilic Allylation by Allylrhodium Chain Walking
Groves, Alistair,Martínez, Jose I.,Smith, Joshua J.,Lam, Hon Wai
, p. 13432 - 13436 (2018/09/21)
Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and with an imine to give Z-homoallylic alcohols and amines, respectively.
Diastereoselective formation of 2,3,4,5-tetrasubstituted tetrahydrofurans by a Lewis acid promoted addition of C3-substituted 1,3-bis(silyl)propenes to aldehydes
Borg, Tessie,Timmer, Brian,Somfai, Peter
, p. 3916 - 3918 (2013/07/25)
A mild, efficient, Lewis acid promoted addition of C3-substituted 1,3-bis(silyl)propenes to aldehydes to provide the corresponding 2,3,4,5-tetrasubstituted tetrahydrofurans in excellent stereoselectivity is reported.
(E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne-yne metathesis/semi-reduction
Lacombe, Fabrice,Radkowski, Karin,Seidel, Günter,Fürstner, Alois
, p. 7315 - 7324 (2007/10/03)
A concise, practical and stereoselective entry into macrocyclic (E)-alkenes is outlined comprising a sequence of ring closing alkyne metathesis (RCAM), trans-selective hydrosilylation of the resulting cycloalkynes catalyzed by [Cp*Ru(MeCN)3]PF6, and a protodesilylation of the ensuing vinylsilanes with AgF in aq. THF/MeOH. Moreover, the first examples of intramolecular enyne-yne metathesis reactions catalyzed by the Schrock alkylidyne complex (tBuO)3WCCMe3 are reported; the resulting cyclic enynes can be converted along similar lines into the corresponding (E,E)-configured 1,3-dienes in good overall yields. Cycloalkyne 4 and the (E)-configured cyclic olefins 6 and 21 were characterized by X-ray crystallography.
STEREOSELECTIVE ADDITION OF α-CHLORO ALLYLIC CHROMIUM REAGENTS TO ALDEHYDES
Takai, Kazuhiko,Kataoka, Yasutaka,Utimoto, Kiitiro
, p. 4389 - 4392 (2007/10/02)
Treatment of a solution of 1,1-dichloro-2-butene and benzaldehyde with CrCl2 in THF-DMF at 25 deg C for 1 h gave threo-(Z)-4-chloro-2-methyl-1-phenyl-3-buten-1-ol in 96percent yield under high stereocontrol.
