Neighboring Hydroxyl Group-Assisted Allylboration and Lewis Acid-Mediated Carbonyl-Ene Reaction for Access to a Hapalindole Cyclohexane Core with Multiple Contiguous Stereogenic Centers

A neighboring hydroxyl group-assisted allylboration of 3-indolyl ketones with γ,γ-disubstituted allylboronic acids is reported, affording various 3-indolyl-substituted homoallylic alcohols in good yields with excellent diastereoselectivies (up to >20:1 dr). The hydroxyl group not only played a vi...

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Published inJournal of organic chemistry Vol. 84; no. 3; pp. 1605 - 1613
Main Authors Li, Lu, Yang, Zhao, Yang, Jiao, Zhang, Quanzheng, Tan, Qiuyuan, Zhang, Changhui, Zhang, Min
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BRONSTED ACID
NATURAL-PRODUCTS
IMINES
ALLYLATION
STEREOSELECTIVE ALLYLBORATION
CATALYTIC ENANTIOSELECTIVE ALLYLBORATION
ALDEHYDES
FLUORINATED ALCOHOLS
CROTYLBORATION
ALKALOIDS
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Summary:A neighboring hydroxyl group-assisted allylboration of 3-indolyl ketones with γ,γ-disubstituted allylboronic acids is reported, affording various 3-indolyl-substituted homoallylic alcohols in good yields with excellent diastereoselectivies (up to >20:1 dr). The hydroxyl group not only played a vital role in the challenging allylboration but was elaborated for the subsequent construction of a hapalindole cyclohexane core by a highly diastereoselective Lewis acid-catalyzed carbonyl-ene reaction. In the overall process, four contiguous stereogenic centers including two quaternary stereogenic centers were installed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02712