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| Type |
Poster Presentation |
| Area |
Medicinal Chemistry |
| Room No. |
Exhibition Hall 2 |
| Time |
4월 18일 (목요일) 11:00~12:30 |
| Code |
MEDI.P-409 |
| Subject |
Diastereoselective Synthesis of 1-Aminoindanes via Rhodium(III) Catalyzed C-H Activation |
| Authors |
Heeyoung Lee, Daeun Jeoung, In Su Kim*
School of Pharmacy, Sungkyunkwan University, Korea
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| Abstract |
Indane has been recognized as an important structural motif in organic synthesis and medicinal chemistry. Particularly, 1-aminoindanes have attracted considerable attention by virtue of their interesting biological properties, such as anti-inflammatory, analgesic, antipyretic, anticonvulsant, anti-leukemic, anti-Parkinson and etc. Therefore, a range of 1-aminoindane derivatives have been synthesized and evaluated for their clinical applications. In this context, imine directing groups have been widely used for new C−C bond formation reactions with various unsaturates such as alkenes, alkynes, and allenes. Additionally, Re(I) and Ru(II) catalysts were also employed in C−H functionalization of ketimines with alkynes and allenes to deliver the corresponding 1-aminoindenes and 1-aminoindanes, respectively. Moreover, Nishimura disclosed the Ir(I)-catalyzed stereoselective annulation of cyclic N-sulfonyl and N-acyl ketimines with 1,3-dienes to yield spiroaminoindane derivatives. Despite of great progress on the coupling reaction between imines and π-unsaturates, examples of annulation reaction using internal alkenes with high diastereoselectivity are still unexplored. In continuation of our recent works on the catalytic sp2 and sp3 C−H functionalizations using internal olefins including maleimides, we herein describe the Rh(III)-catalyzed diastereoselective formation of 1-aminoindanes using N-sulfonyl aldimines and various olefins. |
| E-mail |
yong7173@naver.com |
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123rd General Meeting of the KCS