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RSC Advances
DOI: 10.1039/C5RA13267C
Comprehensive training platform of specialized laboratory,
College of Chemistry, Sichuan University for NMR and HRMS
analysis.
Table 4 Substrate scope of the domino PFLꢀcatalyzed reactiona
30
Notes and references
Key Laboratory of Green Chemistry and Technology, Ministry of
Education, College of Chemistry, Sichuan University, Chengdu, 610064,
35 P. R. China. Tel. & Fax: (86)ꢀ28ꢀ85415886
Eꢀmail: wnchem@scu.edu.cn (N. Wang), xqyu@scu.edu.cn(X.ꢀQ.Yu)
† Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/b000000x/
40 ‡ Footnotes should appear here. These might include comments relevant
to but not central to the matter under discussion, limited experimental and
spectral data, and crystallographic data.
a
Reaction conditions: 1 (1 mmol), 2 (5 mmol), PFL (200 mg),
dichloromethane (4.75 mL), H2O (0.25 mL) were added to a 25 mL
roundꢀbottom flask, and shaken at 200 rpm at 30 °C for 24 h. b Isolated
yields.
45
50
55
60
65
1
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2
3
4
5
6
Scheme 2 Probable mechanism for the lipaseꢀcontrolled regioselective
domino reaction.
7
8
9
5
Conclusions
In conclusion, a series of 2Hꢀchromenones and 2ꢀhydroxyꢀ2Hꢀ
chromenones were synthesized using cycloꢀ1,3ꢀdihexanone and
α,βꢀunsaturated aldehyde as starting materials via BPLꢀ or PFLꢀ
70 10 (a) C. Huber, J. Mpreau, J. Batany, A. Duboc, J.ꢀP. Hurvois, J.ꢀL.
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10 catalyzed domino reaction respectively. In the present work,
lipase promoted regioselectivity for domino reaction is reported
for the first time. It is meaningful to find that lipases show such
powerful regioselectivity in domino reaction. After optimization,
several substrates participated in the reactions smoothly and
15 provided the target products in acceptable to excellent yield
through the lipaseꢀcatalyzed domino reactions. As a new example
of enzyme promiscuity, it expands the applications of lipases in
organic synthesis. However, further study on the mechanism of
the reaction is currently being conducted in our laboratory.
20
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Acknowledgment
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We gratefully acknowledge the financial support of the National
Program on Key Basic Research Project of China (973 Program,
25 2013CB328900) and the National Natural Science Foundation of
China (No. 21321061 and J1310008). We also thank
90
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