Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji-Trost Allylation of N-tert-Butanesulfinyl Imines

Rafid S. Dawood; Irene Georgiou; Ross P. Wilkie; William Lewis; Robert A. Stockman

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Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji-Trost Allylation of N-tert-Butanesulfinyl Imines

机译：通过Tsuji-Trost-丁磺酰基亚胺的Tsuji-Trost烯丙基化学合成含吡咯烷的化学支架的不对称合成

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摘要

A simple and efficient asymmetric synthesis of novel sp3-rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesulfinamide as a chiral auxiliary to perform an asymmetric Tsuji-Trost allylation, with subsequent cross-metathesis with an acrylate ester and reduction of the sulfinimine/cyclisation of the resulting amine giving the pyrrolidine scaffolds in high yields and diastereoselectivites. By removing the chiral auxiliary and functionalising the ester group, the resulting scaffold core can be further derivatised.

机译：描述了一种简单富有高效的非对称合成从简单酮开始的五个步骤的新型SP3富含吡咯烷化学支架。关键步骤涉及使用叔丁磺胺酰胺作为手性助剂，以进行不对称的Tsuji-rtost烯丙基化，随后具有丙烯酸酯酯的交叉复位，并将所得胺的亚氨基胺/环化的降低给予吡咯烷基的支架高产和降低非对映射性。通过除去手性助剂和官能化酯基团，可以进一步衍生产生的支架核心。

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来源
《Chemistry: A European journal》 |2017年第46期|共6页
作者
Rafid S. Dawood; Irene Georgiou; Ross P. Wilkie; William Lewis; Robert A. Stockman;
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作者单位

School of Chemistry University of Nottingham NG7 2RD (UK) Fax: (+44) 115-9513564;

School of Chemistry University of Nottingham NG7 2RD (UK) Fax: (+44) 115-9513564;

School of Chemistry University of Nottingham NG7 2RD (UK) Fax: (+44) 115-9513564;

School of Chemistry University of Nottingham NG7 2RD (UK) Fax: (+44) 115-9513564;

School of Chemistry University of Nottingham NG7 2RD (UK) Fax: (+44) 115-9513564;

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
asymmetric synthesis; imines; Michael addition; pyrrolidines; sulfur;

机译：不对称合成;亚胺;迈克尔加法;吡咯烷;硫;

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1. Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji-Trost Allylation of N-tert-Butanesulfinyl Imines [J] . Rafid S. Dawood, Irene Georgiou, Ross P. Wilkie, Chemistry: A European journal . 2017,第46期

机译：通过Tsuji-Trost-丁磺酰基亚胺的Tsuji-Trost烯丙基化学合成含吡咯烷的化学支架的不对称合成
2. Remarkable salt effect on in-mediated allylation of N-tert-butanesulfinyl imines in aqueous media: Highly practical asymmetric synthesis of chiral homoallylic amines and isoindolinones [J] . Sun XW, Liu M, Xu MH, Organic letters . 2008,第6期

机译：盐对水介质中N-叔丁亚磺酰基亚胺介导的烯丙基化的影响：手性均烯丙基胺和异吲哚啉酮的高度实用的不对称合成
3. Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: dual stereocontrol with nearly perfect diastereoselectivity [J] . Yi-Shuang Zhao, Qiang Liu, Ping Tian, Organic & biomolecular chemistry . 2015,第14期

机译：铜催化的手性N-叔丁烷亚磺酰基亚胺的不对称烯丙基化：具有几乎完美的非对映选择性的双重立体控制
4. Pd-BEt_3 Promoted Nucleophilic Allylation of Imines and N,O-Acetals [C] . Masamichi Shimizu, Toshiya Watanabe, Mariko Hashimoto, Symposium on Organometallic Chemistry . 2004

机译：PD-BET_3促进亚胺的亲核烯丙基，N，O-缩醛
5. New methods for the synthesis of α-amino acid derivatives from N-tert-butanesulfinyl imines and the synthesis and application of novel amino acid based N-tert-butanesulfinyl amide organocatalysts [D] . Herbage, Melissa Ann 2009

机译：由N-叔丁亚磺酰基亚胺合成α-氨基酸衍生物的新方法以及基于氨基酸的新型N-叔丁亚磺酰基酰胺有机催化剂的合成与应用
6. A Highly Stereoselective Addition of Lithiated Ynamides to Ellman–Davis Chiral N-tert-Butanesulfinyl Imines [O] . Xiao-Na Wang, Richard P. Hsung, Rui Qi, -1

机译：对Ellman-Davis手性N-叔丁烷亚磺酰基亚胺的锂酰胺的高度立体选择性加成
7. Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines [O] . Dawood, Rafid S., Georgiou, Irene, Wilkie, Ross P., 2017

机译：N-叔丁烷亚磺酰基亚胺的Tsuji-Trost烯丙基化反应不对称合成含吡咯烷的化学支架

Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji-Trost Allylation of N-tert-Butanesulfinyl Imines

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