Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 20, Pages 3167-3172Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600520
Keywords
asymmetric synthesis; azabenzonorbornadienes; carboxylic acids; co-catalysts; ring opening reaction
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Funding
- National Natural Science Foundation of China [21572198, 21362043, 21302162]
- Government of Yunnan Province [ZB2015012]
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The palladium/silver (Pd/Ag) co-catalytic system was found to be effective for the enantioselective ring opening reactions of the low reactive azabenzonorbornadienes with weak nucleophilic carboxylic acids. Both aryl and alkyl carboxylic acids are suitable nucleophiles and afforded the cis ring opening products in good yields with excellent enantioselectivities. The absolute configuration of one of the products has been confirmed by X-ray crystal structure analysis, and a plausible reaction pathway is proposed.
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