Phosphine-catalysed asymmetric dearomative formal [4+2] cycloadditions of 3-benzofuranyl vinyl ketones†,Chemical Communications

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Phosphine-catalysed asymmetric dearomative formal [4+2] cycloadditions of 3-benzofuranyl vinyl ketones†
Chemical Communications ( IF 4.3 ) Pub Date : 2019-02-15 00:00:00 , DOI: 10.1039/c9cc00386j
Ben-Xian Xiao _{1,

2,

3,

4,

5} , Bo Jiang _{1,

2,

3,

4,

5} , Xue Song _{1,

2,

3,

4,

5} , Wei Du _{1,

2,

3,

4,

5} , Ying-Chun Chen _{1,

2,

3,

4,

5}

Affiliation

In contrast to the catalytic asymmetric dearomative reactions of indole substrates, those of the analogous benzofuran derivatives have been less explored. Here we report that the stereoselective domino Rauhut–Currier/Michael addition process of 3-benzofuranyl vinyl ketones and 3-olefinic (7-aza)oxindoles can be realised via catalysis by a chiral bifunctional phosphine, furnishing the previously unreported direct asymmetric dearomative reaction of benzofuran substrates tethered to a carbonyl group in a formal [4+2] cycloaddition manner. An array of hydrodibenzofuran derivatives with dense substitutions is generally constructed with excellent diastereoselectivity and enantioselectivity (up to >19 : 1 dr, >99% ee).

中文翻译：

膦催化的3-苯并呋喃基乙烯基酮的不对称脱芳香性正[4 + 2]环加成反应†

与吲哚底物的催化不对称脱芳香反应相反，类似苯并呋喃衍生物的反应很少被研究。在这里我们报告说，3-苯并呋喃基乙烯基酮和3-烯烃（7-氮杂）恶吲哚的立体选择性多米诺骨牌的Rauhut-Currier / Michael加成过程可以通过手性双官能膦催化来实现，从而提供了以前未报道的直接的不对称脱芳香反应。苯并呋喃底物以正式的[4 + 2]环加成方式束缚在羰基上。通常以优异的非对映选择性和对映选择性（高达> 19：1 dr，> 99％ee）构建一系列具有高取代度的氢二苯并呋喃衍生物。

更新日期：2019-02-15

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