One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence

Lu Hong; Zhang Huan-Xin; Tan Chang-Yin; Liu Jin-Yu; Wei Hao; Xu Peng-Fei

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One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence

机译：通过一般迈克尔添加/氯化/亲核取代序列通过一般迈克尔加法/亲核替代序列的一锅不对称合成螺吡唑啉酮连接环丙烷和苯并呋喃

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A sequential and general strategy has been successfully developed for the synthesis of spiropyrazolone scaffolds. This intriguing transformation of the asymmetric multicomponent catalysis process was realized with the combination of Michael addition/chlorination/nucleophilic substitution in a one-pot sequence, giving rise to a series of spiropyrazolones with fully substituted cyclopropanes and spiro-dihydrobenzofurans containing continuous stereogenic centers in good yields with excellent stereoselectivities.

机译：已成功开发了一种顺序和一般的策略，用于螺吡唑酮支架的合成。通过迈克尔添加/氯化/亲核取代的组合在单罐序列中实现了不对称多组分催化过程的这种有趣转化，从而产生了一系列螺丝唑酮，其具有完全取代的环丙烷和螺二氢呋喃脲，含有连续立体中心的良好产量具有优异的立体化。

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《The Journal of Organic Chemistry》 |2019年第16期|共14页
作者
Lu Hong; Zhang Huan-Xin; Tan Chang-Yin; Liu Jin-Yu; Wei Hao; Xu Peng-Fei;
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作者单位

Lanzhou Univ Sch Chem &

Chem Engn State Key Lab Appl Organ Chem Lanzhou 730000 Gansu Peoples R China;

Lanzhou Univ Sch Chem &

Chem Engn State Key Lab Appl Organ Chem Lanzhou 730000 Gansu Peoples R China;

Lanzhou Univ Sch Chem &

Chem Engn State Key Lab Appl Organ Chem Lanzhou 730000 Gansu Peoples R China;

Lanzhou Univ Sch Chem &

Chem Engn State Key Lab Appl Organ Chem Lanzhou 730000 Gansu Peoples R China;

Northwest Univ Coll Chem &

Mat Sci Natl Demonstrat Ctr Expt Chem Educ Key Lab Synthet &

Nat Funct Mol Chem Minist Educ Xian 710127 Shaanxi Peoples R China;

Lanzhou Univ Sch Chem &

Chem Engn State Key Lab Appl Organ Chem Lanzhou 730000 Gansu Peoples R China;

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正文语种 eng
中图分类有机化学;
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1. One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence [J] . Lu Hong, Zhang Huan-Xin, Tan Chang-Yin, The Journal of Organic Chemistry . 2019,第16期

机译：通过一般迈克尔添加/氯化/亲核取代序列通过一般迈克尔加法/亲核替代序列的一锅不对称合成螺吡唑啉酮连接环丙烷和苯并呋喃
2. Asymmetric nucleophilic #alpha#-amino-acylation with metalated chiral amino nitriles: enantioselective synthesis of 3-substituted 5-amino-4-oxo-esters via asymmetric Michael addition [J] . Dieter Enders, John P. Shilvock, Gerhard Raabe Journal of the Chemical Society, Perkin Transactions 1 . 1999,第12期

机译：金属手性氨基腈的不对称亲核＃alpha＃-氨基酰化：通过不对称迈克尔加成反应对映体选择性合成3-取代的5-氨基-4-氧代酯
3. Asymmetric nucleophilic #alpha#-amino-acylation with metalated chiral amino niriles:enantio-selective synthesis of 3-substituted 5-amino-4-oxo-esters via asymmetric Michael addition [J] . Enders Dieter, Shilvock John P. Journal of the Chemical Society. Dalton Transactions . 1999,第12期

机译：金属手性氨基腈的不对称亲核＃alpha＃-氨基酰化：通过不对称迈克尔加成反应的对映体选择性合成3-取代的5-氨基-4-氧代酯
4. Michael Addition Reactions between Nucleophilic GlycineEquivalents and Acrylic Acid Derivatives as a Practicaland Generalized Approach to the Asymmetric Synthesisof II-Substituted-a-Amino Acids [C] . Vadim A. Soloshonok, Hisanori Ueki, Trevor K. Ellis ACS symposium asymmetric synthesis and application of α-amino acids . 2009

机译：亲核糖糖糖尿剂与丙烯酸衍生物之间的迈克尔添加反应作为不对称合成的不对称 - A-氨基酸的不对称方法的普遍化方法
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. Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution [O] . Mei Kee Kam, Akira Sugiyama, Ryouta Kawanishi, 2020

机译：通过对映选择性脱羧氯化和随后的亲核取代的叔α-羟基酮的不对称合成
7. One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence [O] . -1

机译：通过一般迈克尔添加/氯化/亲核取代序列通过一般迈克尔加法/亲核替代序列的一锅不对称合成螺吡唑啉酮连接环丙烷和苯并呋喃

One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence

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