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Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane
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  • Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane
  • Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane
저자명
Cha. Jin-Soon,Noh. Min-Yeong
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2010년|31권 4호|pp.840-844 (5 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

The new MPV type reagent, Al-methanesulfonyldiisobutylalane ($DIBAO_3SCH_3$), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined in order to find out a new reducing system with high selectivity in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones and epoxides. The reagent exhibits a unique reducing applicability in organic synthesis. Thus, the reagent can achieve a clean 1,2-reduction of $alpha,eta$-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in 100% purity. In addition, the reagent shows an excellent regioselectivity in the ring-opening reaction of epoxides. Finally, $DIBAO_3SCH_3$ shows a high stereoselectivity in the reduction of cyclic ketones to produce the thermodynamically more stable epimers exclusively.