Catalytic Asymmetric Nucleophilic Addition of 3‑Vinyl Indoles to Imines

The 3-vinyl indole is used as a nucleophile to react with aromatic and aliphatic imines. Chiral 3-substituted indoles bearing multiple functional groups are produced with up to 99% yield, a 98:2 E/Z ratio, and 97% ee. A possible mechanism is proposed to explain the observed stereoselectivities. This...

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Published inOrganic letters Vol. 18; no. 15; pp. 3874 - 3877
Main Authors Xue, Jia-Hui, Shi, Ming, Yu, Feng, Li, Xiao-Yun, Ren, Wen, Fu, Li-Na, Guo, Qi-Xiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.08.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
DIELS-ALDER REACTIONS
ALKYLATION
CHIRAL BRONSTED ACID
GENERATION
DERIVATIVES
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Summary:The 3-vinyl indole is used as a nucleophile to react with aromatic and aliphatic imines. Chiral 3-substituted indoles bearing multiple functional groups are produced with up to 99% yield, a 98:2 E/Z ratio, and 97% ee. A possible mechanism is proposed to explain the observed stereoselectivities. This strategy provides an efficient way for the preparation of novel chiral 3-substituted indoles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01880