Phosphine-catalysed α-umpolung addition of nucleophiles to δ-acetoxy allenoates: stereoselective synthesis of 2,4-dienoates†,Organic & Biomolecular Chemistry

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Phosphine-catalysed α-umpolung addition of nucleophiles to δ-acetoxy allenoates: stereoselective synthesis of 2,4-dienoates†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-06-07 00:00:00 , DOI: 10.1039/c8ob00933c
Yading Hou _{1,

2,

3,

4,

5} , Yuwen Zhang _{1,

2,

3,

4,

5} , Xiaofeng Tong _{1,

2,

3,

4,

5}

Affiliation

The first example of phosphine-catalyzed α-umpolung addition of nucleophiles to allenoates is described, which features the use of δ-acetoxy allenoate to generate a 3-phosphonium-2,4-dienoate intermediate, thus facilitating the α-umpolung addition of nucleophiles. Both sulfinate and diarylphosphine oxide are competitive nucleophiles, affording highly activated conjugated dienes with good to excellent stereoselectivities.

中文翻译：

膦催化的亲核试剂在δ-乙酰氧基烯酸酯中的α-聚醚砜加成反应：2,4-二烯酸酯的立体选择性合成†

描述了膦催化亲核试剂向亲核酸酯中添加α-聚醚酮的第一个实例，其特征在于使用δ-乙酰氧基烯丙基酯生成3-phosph-2,4-二烯酸酯中间体，从而有利于亲核试剂的α-聚醚仑加成。。亚磺酸盐和二芳基膦氧化物都是竞争性亲核试剂，可提供高度活化的共轭二烯，具有良好或优异的立体选择性。

更新日期：2018-06-07

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