Part I: Desymmetrization of cyclic olefins via asymmetric Heck reaction and hydroarylation. Part II: Fast Suzuki coupling of aryl tosylates

Part 1. Asymmetric Heck reaction of substituted cyclopentenes gave one stereoisomer in excellent enantio- and diastereoselectivities. The high selectivity as unprecedented in Heck reaction. (R)-Xyl-SDP(O) was uniquely effective as chiral ligand. Various aryl triflates can be used. The same catalyst...

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Bibliographic Details
Main Author: Liu, Sijia
Other Authors: Steve Zhou
Format: Theses and Dissertations
Language:English
Published: 2014
Subjects:
Online Access:https://hdl.handle.net/10356/55382
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Institution: Nanyang Technological University
Language: English
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Summary:Part 1. Asymmetric Heck reaction of substituted cyclopentenes gave one stereoisomer in excellent enantio- and diastereoselectivities. The high selectivity as unprecedented in Heck reaction. (R)-Xyl-SDP(O) was uniquely effective as chiral ligand. Various aryl triflates can be used. The same catalyst can be applied to asymmetric hydroarylation of norbornene and other bicyclic derivatives in excellent ee. Part 2. A general procedure for fast Suzuki coupling of heteroaryl tosylates as developed. Most major families of heteroaryls can couple at room temperature. The method is generally applicable to major families of heterocyclic substrates, and most reactions completed within minutes to hours.