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Allyl Transfer to Aldehydes and Ketones by Bronsted Acid Activation of Allyl and Crotyl 1,3,2-Dioxazaborolidines

  作者 REILLY MAUREEN K; RYCHNOVSKY SCOTT D  
  选自 期刊  Organic Letters;  卷期  2010年12-21;  页码  4892-4895  
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[摘要]Alkyl dioxazaborolidines are air-stable and often crystalline organoboranes. A variety of Bronsted acids activate allyl dioxazaborolidines to generate reactive allyl-transfer reagents in situ. These reagents add to aldehydes and ketones to generate the corresponding alcohols in good yields under mild conditions. The E- and Z-crotyl reagents react diastereoselectively with aldehydes and ketones to produce anti and syn adducts, respectively, a result consistent with a cyclic transition state (type I mechanism).

 
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