Asymmetric Conjugate Addition of Malonate Esters to α,β-Unsaturated N-Sulfonyl Imines: An Expeditious Route to Chiral δ-Aminoesters and Piperidones

Miguel Espinosa; Gonzalo Blay; Luz Cardona; José R. Pedro

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Asymmetric Conjugate Addition of Malonate Esters to α,β-Unsaturated N-Sulfonyl Imines: An Expeditious Route to Chiral δ-Aminoesters and Piperidones

机译：丙二酸酯向α，β-不饱和N-磺酰基亚胺的不对称共轭加成：手性δ-氨基酯和哌啶酮的快速途径

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The asymmetric conjugate addition of malonate esters to α,β-unsaturated N-sulfonyl imines is catalyzed by PyBOX/La(OTf)_3 complexes in the presence of 4 A MS. The reaction gives the corresponding E enamines bearing a stereogenic center at the allylic position with good yields and enantiomeric ratios up to 97:3. This reaction provides a synthetic entry to chiral δ-aminoesters and piperidones.

机译：在4 A MS的存在下，PyBOX / La（OTf）_3配合物催化丙二酸酯向α，β-不饱和N-磺酰基亚胺的不对称共轭加成反应。反应得到相应的E烯胺，其在烯丙基位置带有立体异构中心，具有良好的产率和高达97：3的对映体比例。该反应提供了手性δ-氨基酯和哌啶酮的合成入口。

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《Chemistry: A European journal》 |2013年第44期|共6页
作者
Miguel Espinosa; Gonzalo Blay; Luz Cardona; José R. Pedro;
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正文语种 eng
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amino acids; asymmetric catalysis; carbanions; conjugate addition; imino compounds;

机译：氨基酸;不对称催化;碳负离子;共轭加成;亚氨基化合物;

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1. Asymmetric Conjugate Addition of Malonate Esters to α,β-Unsaturated N-Sulfonyl Imines: An Expeditious Route to Chiral δ-Aminoesters and Piperidones [J] . Miguel Espinosa, Gonzalo Blay, Luz Cardona, Chemistry: A European journal . 2013,第44期

机译：丙二酸酯向α，β-不饱和N-磺酰基亚胺的不对称共轭加成：手性δ-氨基酯和哌啶酮的快速途径
2. Silver/ThioClickFerrophos complex as an effective catalyst for asymmetric conjugate addition of glycine imino ester to unsaturated malonates and α-enones [J] . Konno T., Watanabe S., Takahashi T., Organic letters . 2013,第17期

机译：银/ ThioClickFerrophos配合物可有效地将甘氨酸亚氨基酯不对称共轭加成到不饱和丙二酸酯和α-烯酮上
3. An eco-friendly asymmetric organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes: Application on the synthesis of chiral indoles [J] . Feu K.S., Deobald A.M., Narayanaperumal S., European journal of organic chemistry . 2013,第26期

机译：丙二酸酯向α，β-不饱和醛的生态友好型不对称有机催化共轭加成：在手性吲哚合成中的应用
4. N-Boc-L-Val-Connected Amidophosphane-Copper(I) Catalyst in Asymmetric Conjugate Addition of Dialkylzinc to Unsaturated Imines [C] . Takahiro Soeta, Masami Kuriyama, Kiyoshi Totnioka Symposium on Organometallic Chemistry . 2004

机译：N-Boc-L-Val连接的酰胺磷酸 - 铜（I）催化剂在不对称的缀合物中加入二烷基锌到不饱和亚胺
5. Asymmetric synthesis of C-1 substituted cocaine analogues using sulfinimine (N-sulfinyl imine) chemistry and vinylaluminum addition to sulfinimines (n-sulfinyl imines) for the asymmetric synthesis of alpha-substituted-beta-amino esters. [D] . Gaddiraju, Narendra Varma. 2013

机译：不对称合成C-1取代可卡因类似物，使用亚磺胺（N-亚磺酰基亚胺）化学物质和乙烯基铝加成亚磺胺（n-亚磺酰基亚胺）进行α-取代-β-氨基酯的不对称合成。
6. Chiral N-Phosphonyl Imine Chemistry: Asymmetric Additions of Ester Enolates for the Synthesis of β-Amino Acids [O] . Jianlin Han, Teng Ai, Thao Nguyen, -1

机译：手性N-膦酰基亚胺化学：酯烯醇盐的不对称加成用于合成β-氨基酸
7. Corrigendum: Asymmetric Conjugate Addition of Malonate Esters to α,β-UnsaturatedN-Sulfonyl Imines: An Expeditious Route to Chiral δ-Aminoesters and Piperidones [O] . Miguel Espinosa, Gonzalo Blay, Luz Cardona, 2013

机译：静脉静脉：向α，β-不饱和 - 磺酰基亚内的不对称缀合物加入α，β-不饱和 - 磺酰基亚内膜：迅速的手性δ-氨基酯和哌啶途径

Asymmetric Conjugate Addition of Malonate Esters to α,β-Unsaturated N-Sulfonyl Imines: An Expeditious Route to Chiral δ-Aminoesters and Piperidones

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