Previous studies in our group showed that strained rings could be easily functionalized and ring-opened to access acyclic molecular frameworks bearing stereocontrolled quaternary centers.1 Following those pioneering works and inspired by the concept of metal-walk,2 we investigated the behaviour of 2-vinylcyclopropylmethanol derivatives in Heck reactions (Scheme 1). We are pleased to report a highly modular and diastereoselective approach that enabled the access to most stereoisomers, in only three catalytic steps from easily accessible starting materials.3
Scheme 1: Rapid and modular access to complex acyclic systems
References:
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2. a) A. Vasseur, J. Bruffaerts, I. Marek, Nature Chem. 2016, 8, 209 ; b) T.-S. Mei, H. H. Patel, M. S. Sigman, Nature 2014, 508, 340.
3. D. Didier, P.-O. Delaye, M. Simaan, B. Island, G. Eppe, H. Eijsberg, A. Kleiner, P. Knochel, I. Marek, Chem. Eur. J. 2014, 20, 1038.