Canova, Sophie published the artcileRearrangement of Homoallylic Alcohols Induced by DAST, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Organic Letters (2006), 8(10), 2091-2094, database is CAplus and MEDLINE.
Nonracemic α-substituted-β-methoxy homoallylic alcs. RCH(OH)CH(OMe)CH:CH2 [R = TBDPSOCH2CH2, PhCH2OCH2CH2, (R)-TBDPSOCH2CHMe, (S)-TBDPSOCH2CHMeCH2; TBDPS = Me3CSi(Ph)2; (I)] undergo diethylaminosulfur trifluoride (DAST)-mediated fluorination and rearrangement on silica gel to provide β,γ-unsaturated aldehydes RCH(CHO)CH:CH2 [R = TBDPSOCH2CH2, PhCH2OCH2CH2, (R)-TBDPSOCH2CHMe, (S)-TBDPSOCH2CHMeCH2; (II)] in 76-90% yields and with good transfer of chirality. II are unstable to prolonged treatment with silica gel, rearranging to the corresponding α,β-unsaturated aldehydes, and are reduced with sodium borohydride to the primary homoallylic alcs. RCH(CH2OH)CH:CH2 [R = TBDPSOCH2CH2, PhCH2OCH2CH2, (R)-TBDPSOCH2CHMe, (S)-TBDPSOCH2CHMeCH2]. The racemic homoallylic alcs. PhCH2CH(OH)CH2CH:CH2 and TBDPSOCH2CH2CH(OH)CH2CH:CH2 lacking an α-methoxy substituent undergo fluorination without rearrangement; reaction of the secondary alc. derived from I [R = (R)-TBDPSOCH2CHMe] by hydrogenation of the olefin with DAST yields a complex mixture
Organic Letters published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.
Referemce:
https://en.wikipedia.org/wiki/Ether,
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