A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

作者： Dhevalapally B. Ramachary , M. Shiva Prasad , R. Madhavachary

关键词:

摘要: A general approach to the high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans as drug intermediates was achieved through cascade Barbas–Michael and acetalization (BMA) reactions on 2-(2-nitrovinyl)phenols with aldehydes in presence a catalytic amount (R)-DPPOTMS PhCO2H. Herein, we have also demonstrated application BMA products functionalized chromanes chromenes very good yields high optical purity, which are useful compounds medicinal chemistry.

参考文章(40)

Xueyong Zhu, Fujie Tanaka, Richard A. Lerner, Carlos F. Barbas III, Ian A. Wilson, Direct observation of an enamine intermediate in amine catalysis Journal of the American Chemical Society. ,vol. 131, pp. 18206- 18207 ,(2009) , 10.1021/JA907271A

Steven A Buckner, Ivan Milicic, Anthony Daza, Rachel Davis-Taber, Victoria E.S Scott, James P Sullivan, Jorge D Brioni, Pharmacological and molecular analysis of ATP-sensitive K+ channels in the pig and human detrusor European Journal of Pharmacology. ,vol. 400, pp. 287- 295 ,(2000) , 10.1016/S0014-2999(00)00388-5

Alessio Coi, Anna Maria Bianucci, Vincenzo Calderone, Lara Testai, Maria Digiacomo, Simona Rapposelli, Aldo Balsamo, Predictive models, based on classification algorithms, for compounds potentially active as mitochondrial ATP-sensitive potassium channel openers. Bioorganic & Medicinal Chemistry. ,vol. 17, pp. 5565- 5571 ,(2009) , 10.1016/J.BMC.2009.06.028

Bernhard Lesch, Stefan Bräse, A Short, Atom-Economical Entry to Tetrahydroxanthenones Angewandte Chemie International Edition. ,vol. 43, pp. 115- 118 ,(2004) , 10.1002/ANIE.200352154

Benjamin List, Peter Pojarliev, Harry J. Martin, Efficient Proline-Catalyzed Michael Additions of Unmodified Ketones to Nitro Olefins Organic Letters. ,vol. 3, pp. 2423- 2425 ,(2001) , 10.1021/OL015799D

Dhevalapally B. Ramachary, Y. Vijayendar Reddy, A General Approach to Chiral Building Blocks via Direct Amino Acid-Catalyzed Cascade Three-Component Reductive Alkylations: Formal Total Synthesis of HIV-1 Protease Inhibitors, Antibiotic Agglomerins, Brefeldin A, and (R)-γ-Hexanolide Journal of Organic Chemistry. ,vol. 75, pp. 74- 85 ,(2010) , 10.1021/JO901799N

Juan M Betancort, Kandasamy Sakthivel, Rajeswari Thayumanavan, Carlos F Barbas, Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates Tetrahedron Letters. ,vol. 42, pp. 4441- 4444 ,(2001) , 10.1016/S0040-4039(01)00793-6

Smail Khelili, Xavier Florence, Mourad Bouhadja, Samia Abdelaziz, Nadia Mechouch, Yekhlef Mohamed, Pascal de Tullio, Philippe Lebrun, Bernard Pirotte, Synthesis and activity on rat aorta rings and rat pancreatic beta-cells of ring-opened analogues of benzopyran-type potassium channel activators. Bioorganic & Medicinal Chemistry. ,vol. 16, pp. 6124- 6130 ,(2008) , 10.1016/J.BMC.2008.04.043

Maria C. Breschi, Vincenzo Calderone, Alma Martelli, Filippo Minutolo, Simona Rapposelli, Lara Testai, Federica Tonelli, Aldo Balsamo, New Benzopyran-Based Openers of the Mitochondrial ATP-Sensitive Potassium Channel with Potent Anti-Ischemic Properties Journal of Medicinal Chemistry. ,vol. 49, pp. 7600- 7602 ,(2006) , 10.1021/JM061228L

10.

Vishnumaya, Vinod K. Singh, Highly Enantioselective Water-Compatible Organocatalyst for Michael Reaction of Ketones to Nitroolefins Organic Letters. ,vol. 9, pp. 1117- 1119 ,(2007) , 10.1021/OL070082X

A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

来源期刊

我的账户

A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

来源期刊

相似文章 10

我的账户