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Hokkaido University Collection of Scholarly and Academic Papers >
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1,4-Addition of arylboronic acids to β-aryl-α,β-unsaturated ketones and esters catalyzed by a rhodium(I)-chiraphos complex for catalytic and enantioselective synthesis of selective endothelin A receptor antagonists
| Title: | 1,4-Addition of arylboronic acids to β-aryl-α,β-unsaturated ketones and esters catalyzed by a rhodium(I)-chiraphos complex for catalytic and enantioselective synthesis of selective endothelin A receptor antagonists |
| Authors: | Itoh, Takahiro Browse this author | | Mase, Toshiaki Browse this author | | Nishikata, Takashi Browse this author | | Iyama, Tetsuji Browse this author | | Tachikawa, Hiroto Browse this author | | Kobayashi, Yuri Browse this author | | Yamamoto, Yasunori Browse this author →KAKEN DB | | Miyaura, Norio Browse this author |
| Issue Date: | 9-Oct-2006 |
| Publisher: | Elsevier Ltd |
| Journal Title: | Tetrahedron |
| Volume: | 62 |
| Issue: | 41 |
| Start Page: | 9610 |
| End Page: | 9621 |
| Publisher DOI: | 10.1016/j.tet.2006.07.075 |
| Abstract: | An enantioselective synthesis of acyclic β-diaryl ketones and esters via 1,4-addition of arylboronic acids to β-aryl-α,β-unsaturated ketones or esters is described. The complex in situ prepared from [Rh(nbd)2]BF4 and chiraphos was found to be an excellent catalyst to achieve high enantioselectivities in a range of 83–89% ee for the ketone derivatives and 78–94% ee for tert-butyl β-arylacrylate derivatives. The protocol provided a catalytic method for the enantioselective synthesis of selective endothelin A receptor antagonists (7, 8) reported by SmithKline Beecham and Merck–Banyu. The enantioselection mechanism and efficiency of the chiraphos ligand for β-aryl-α,β-unsaturated ketones and esters are discussed on the basis of results of DFT computational studies on the modes of coordination of the enone substrates to the phenylrhodium(I)–(S,S)-chiraphos complex. |
| Relation: | http://www.sciencedirect.com/science/journal/00404020 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/14775 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 宮浦 憲夫
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