Synthesis of chiral 3-Substituted indanones via an enantioselective reductive-Heck reaction

A Minatti, X Zheng, SL Buchwald

Index: Minatti, Ana; Zheng, Xiaolai; Buchwald, Stephen L. Journal of Organic Chemistry, 2007 , vol. 72, # 24 p. 9253 - 9258

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Citation Number: 67

Abstract

After some preliminary screening studies, our initial reaction conditions for the cyclization of (E)-2'-triflylchalcone 1a (X = OTf) employed a catalyst system comprised of 5 mol % of Pd(OAc) 2 , 10 mol % of (R)-BINAP, and 2 equiv of Hünig's base in DMF at 100 °C (Table 1, entry 1). We observed that the cyclization provided the desired product 2a in 32% yield with an enantiomeric excess of 54%. 9 Variation of the amine base revealed that proton sponge gave the ...