A Combination of Metal and Organic Catalysis: Highly Diastereo- and Enantioselective Construction of Fluorinated 2-Aminocyclopenta[b]pyran Derivatives

An efficient highly diastereo‐ and enantioselective protocol to access optically pure fluorine‐containing 2‐amino‐cyclopenta[b]pyran derivatives using Lewis acid catalysis and organocatalysis sequence has been developed. The corresponding products could be obtained in good to excellent yields with g...

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Published inAdvanced synthesis & catalysis Vol. 357; no. 16-17; pp. 3639 - 3647
Main Authors Peng, Jiahuan, Zhao, Bo-Liang, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 16.11.2015
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
bis(thiazolines)
Catalysis
Chemistry
Chemistry, Applied
Chemistry, Organic
Construction
Derivatives
Fluorination
Lewis acid
Michael addition
Physical Sciences
pyrans
Science & Technology
squaramides
Synthesis
Michael addition
pyrans
squaramides
ASYMMETRIC FLUORINATION
PHARMACEUTICALS
fluorination
BIS(OXAZOLINE)
bis(thiazolines)
asymmetric catalysis
DISCOVERY
NITROALKANES
FRIEDEL-CRAFTS ALKYLATION
AZA-MICHAEL/MICHAEL ADDITION
TRIFLUOROMETHYLATION
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Summary:An efficient highly diastereo‐ and enantioselective protocol to access optically pure fluorine‐containing 2‐amino‐cyclopenta[b]pyran derivatives using Lewis acid catalysis and organocatalysis sequence has been developed. The corresponding products could be obtained in good to excellent yields with good to excellent diastereoselectivity and enantioselectivity (up to 99:1 dr, >99% ee).
Bibliography:National Natural Science Foundation of China - No. nos. 20772006 and 21272024
istex:1548F1E6E581E5651D083AD48090E23DE88FABD0
ArticleID:ADSC201500744
ark:/67375/WNG-LPB10H2W-D
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500744