Enantioselective conjugate addition of N-heterocycles to α, β-enones mediated by diarylprolinols

Letters in Organic Chemistry

Volumn 6, Issue 5, 2009, Pages 397-399

  Fang, Ling ^a   Lin, Aijun ^a   Jia, Xuefeng ^a   Meng, Jie ^a   Wang, Yangnian ^a   Zhu, Chengjian ^a,b  

^a NANJING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric; Benzotriazole; Conjugate addition; Diarylprolinols; Enones; Organocatalysis

Indexed keywords

EID: 69549090124     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809788681248     Document Type: Article

References (23)

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21. 3) δ 158.2, 158.0, 140.3, 138.4, 137.8, 128.5, 127.7, 127.1, 126.6, 113.6, 113.4, 79.6, 76.5, 70.8, 63.6, 55.3, 55.2, 52.0, 33.0
22. 3) δ 4.04 (dd, J = 6.0, 18.0 Hz, 1H), 4.83 (dd, J = 8.0, 18.0 Hz, 1H), 6.71 (dd, J = 6.9, 7.2 Hz, 1H), 7.38-7.40 (m, 1H), 7.46-7.52 (m, 4H), 7.58-7.63 (m, 3H), 8.07 (d, J = 8.4 Hz, 1H), 7.98-8.00 (m, 2H), 8.20-8.18 (m, 2H). HPLC (Chiralpak AD-H, i- PrOH/hexane = 50: 50, flow rate 0.5 ml/min), retention time, 40.6 min (minor), 54.4 min (major).
23. Due to the poor reactive nature of the aromatic enones, iminiumion mechanism was less acceptable.