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Allylic alcohols stereoselective hydroformylation

The general procedure is easy to reproduce and allows stereoselective hydroformylation to be applied to a wide variety of 1,1 disubstituted allylic alcohols. Table 12.1 summarizes the result of o-DPPB-directed stereoselective hydroformylation of several different allylic alcohols, with high levels of stereoinduction. [Pg.229]

Chiou et (d. [81] investigated the hydroformylation-acetalization in the framework of the synthesis of pyrrolidinoindolines and tetrahydrofuranoin-dolines (Scheme 5.89). The hydroformylation occurred in the a-position of the aryl ring. Double cyclization constructed the fused pyrrolidine ring in a stereoselective maimer. Based on this protocol, a variety of pharmacologically important alkaloids were synthesized. By application of the corresponding allyl alcohol as starting material, the THF-based physovenine was prepared. [Pg.461]

Very recently the tandem hydroformylation/acetalization has been used for the synthesis of new synthetically valuable chiral auxiliary derived from camphor. Stereoselective allylation of camphor and subsequent terminal hydroformylation of the resulting homoallylic alcohol affords the 5-lactol auxiliary (camTHP OH) in multigram scale (Scheme 8) [41]. [Pg.79]

The synthesis began with Yb(OTf)3-catalyzed oxymercuration [88] of ho-moallyUc alcohol 204 [89], prepared by asymmetric allylation with Brown s reagent, to generate organomercury chloride 205. Rh(I)-catalyzed formy-lation [90] of 205 in the presence of DABCO (0.5 equiv.) furnished aldehyde 206. Stereoselective crotylation of 206 via Brown s reagent, followed by regioselective Rh(I)-catalyzed hydroformylation provided lactol 203. Dia-... [Pg.178]


See other pages where Allylic alcohols stereoselective hydroformylation is mentioned: [Pg.163]    [Pg.13]    [Pg.79]    [Pg.226]    [Pg.8]    [Pg.155]   
See also in sourсe #XX -- [ Pg.226 ]




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Alcohols, allylic stereoselectivity

Allyl alcohol, hydroformylation

Allyl hydroformylation

Allylation stereoselective

Allylation stereoselectivity

Allylic stereoselective

Hydroformylation alcohols

Hydroformylation stereoselectivity

Hydroformylation, stereoselective

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