|
Type |
Oral Presentation |
Area |
Oral Presentations for Young Scholars in Organic Division |
Room No. |
Room 325A+B |
Time |
THU 09:00-: |
Code |
ORGN.O-1 |
Subject |
Enantioselective Protonation/Nucleophilic Addition and Strecker Reaction Catalyzed by Chiral Oxazaborolidinium Ion |
Authors |
Ki-Tae Kang , Do Hyun Ryu* Department of Chemistry, Sungkyunkwan University, Korea |
Abstract |
A new chiral Brønsted acid derived from carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters with carboxylic acids. Meanwhile, In the presence of a catalytic amount of COBI, aldimine reacted with trimethylsilyl cyanide (TMSCN) to a afford α-aminonitriles in excellent yields and enantioselectivities. The three-component asymmetric process studied here significantly improves upon the original Strecker reaction, and has advantages over previous reactions using unstable imines. High levels of enantioselectivities in the synthesis of α-aminonitrile derivatives with wide substrate generality were obtained via these reactions. The reaction proceeded in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee). |
E-mail |
kkooru11@naver.com |
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