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通过铑（II）催化的C-H插入过程对顺式-2-芳基-3-甲氧基羰基-2,3-二氢苯并呋喃进行对映选择性和非对映选择性合成。

Enantio- and diastereoselective synthesis of cis-2-aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans via the Rh(II)-catalyzed C-H insertion process.

作者信息

Saito Hiroaki, Oishi Hiroyuki, Kitagaki Shinji, Nakamura Seiichi, Anada Masahiro, Hashimoto Shunichi

机构信息

Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

出版信息

Org Lett. 2002 Oct 31;4(22):3887-90. doi: 10.1021/ol0267127.

DOI:10.1021/ol0267127
PMID:12599484
Abstract

[formula: see text] The enantioselective intramolecular C-H insertion reaction of aryldiazoacetates has been explored with use of dirhodium(II) carboxylate catalysts, which incorporate N-phthaloyl- or N-benzene-fused-phthaloyl-(S)-amino acids as chiral bridging ligands. Dirhodium tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, has proven to be the catalyst of choice for this process, providing exclusively cis-2-aryl-3-methoxycarbonyl-2,3-dihydobenzofurans in up to 94% ee.

摘要

[化学式：见正文] 使用羧酸铑（II）催化剂探索了芳基重氮乙酸酯的对映选择性分子内C-H插入反应，该催化剂包含N-邻苯二甲酰基或N-苯并稠合邻苯二甲酰基-（S）-氨基酸作为手性桥连配体。四[（N-邻苯二甲酰基-（S）-叔亮氨酸）]二铑，Rh2（S-PTTL）4，已被证明是该反应的首选催化剂，可提供高达94%ee的纯顺式-2-芳基-3-甲氧基羰基-2,3-二氢苯并呋喃。

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