Journal
ORGANIC LETTERS
Volume 22, Issue 1, Pages 46-51Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03858
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Funding
- National Natural Science Foundation of China (NSFC) [21572047]
- Plan for Scientific Innovation Talents of Henan Province [184200510012]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [20IRTSTHN005]
- Key Project of Science and Technology of Henan Province [192102310412]
- 111 Project [D17007]
- Singapore University of Technology and Design [T1MOE1706]
- Singapore University of Technology and Design (SUTD-MIT IDC grant) [IDG31800104]
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A highly regio- and stereoselective synthesis of functionalized benzofulvenes via Rh(III)-catalyzed cascade reactions of benzoyl acetonitrile/methylsulfone/acetate with propargyl alcohols is presented herein. Mechanistic modeling performed with density functional theory (DFT) calculations suggested that the hydroxyl group and CsOAc played important roles in mediating the 5-membered ring cyclization by forming a very thermodynamically stable Rh(III) intermediate. Another remarkable feature of this transformation is its excellent stereoselectivity in that only E-isomers are obtained.
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