TY - JOUR
T1 - Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3-Methylindoles and Carbonyls
AU - Wani, Imtiyaz Ahmad
AU - Das, Subhomoy
AU - Mondal, Shobhan
AU - Ghorai, Manas K.
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/12/7
Y1 - 2018/12/7
N2 - A highly efficient and stereoselective route to access 1,3-disubstituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles and 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles with excellent stereoselectivity (de, ee >99%) via base mediated ring opening of aziridines/epoxides with 3-methylindoles followed by BF 3 ·OEt 2 catalyzed Pictet-Spengler reaction is accomplished. Interestingly, PTSA promoted cyclization led to the formation of oxidized 3,4-dihydropyrazino[1,2-a]indoles in excellent yields via an unprecedented Pictet-Spengler-detosylation cascade.
AB - A highly efficient and stereoselective route to access 1,3-disubstituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles and 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles with excellent stereoselectivity (de, ee >99%) via base mediated ring opening of aziridines/epoxides with 3-methylindoles followed by BF 3 ·OEt 2 catalyzed Pictet-Spengler reaction is accomplished. Interestingly, PTSA promoted cyclization led to the formation of oxidized 3,4-dihydropyrazino[1,2-a]indoles in excellent yields via an unprecedented Pictet-Spengler-detosylation cascade.
UR - http://www.scopus.com/inward/record.url?scp=85058173898&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b02339
DO - 10.1021/acs.joc.8b02339
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C2 - 30407006
AN - SCOPUS:85058173898
SN - 0022-3263
VL - 83
SP - 14553
EP - 14567
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -