ORGANIC
LETTERS
2
005
Vol. 7, No. 17
769-3771
One-Step Assembly of Functionalized
-Butyrolactones from Benzoins or
Benzaldehydes via an N-Heterocyclic
Carbene-Mediated Tandem Reaction
3
γ
Wei Ye,†,‡ Guanliang Cai, Zeyang Zhuang, Xueshun Jia, and Hongbin Zhai*
‡
†,§
§
,†
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai,
China 200032, Analytical Center, Institute of Chemical Defense, Beijing, China
102205, and Department of Chemistry, Shanghai UniVersity, Shanghai, China 200436
Received June 19, 2005
ABSTRACT
We describe here a direct, efficient, one-step construction of
γ,γ-difunctionalized γ-butyrolactones from benzoins or benzaldehydes via a
tandem reaction promoted by 1,3-dimethyl imidazolin-2-ylidene, an N-heterocyclic carbene (NHC).
Since the isolation and characterization of the stable N-
multicomponent reactions (MCRs) were reported by Nair6
and Ma, respectively.
Having been fascinated by the attractive characteristics of
NHCs, we decided to investigate the reaction of benzoin (1a,
Scheme 1) and methyl acrylate in the presence of 1,3-
1
7
heterocyclic carbene (NHC) species by Arduengo in 1991,
2
there has been considerable attention given to exploring and
developing NHC-mediated organic transformations such as
3
4
benzoin condensation, Stetter reaction, and transesterifi-
5
cation. Recently, several successful cases of NHC-triggered
(4) For selected examples, see: (a) Kerr, M. S.; Read de Alaniz, J.; Rovis,
T. J. Am. Chem. Soc. 2002, 124, 10298. (b) Mattson, A. E.; Bharadwaj, A.
R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314. (c) Kerr, M. S.;
Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876. (d) Kerr, M. S.; Rovis, T.
Synlett 2003, 1934. (e) Ciganek, E. Synthesis 1995, 1311. (f) Pesch, J.;
Harms, K.; Bach, T. Eur. J. Org. Chem. 2004, 2025. (g) Barrett, A. G. M.;
Love, A. C.; Tedeschi, L. Org. Lett. 2004, 6, 3377.
(5) For selected examples, see: (a) Nyce, G. W.; Lamboy, J. A.; Connor,
E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587. (b) Grasa,
G. A.; G u¨ veli, T.; Singh, R.; Nolan, S. P. J. Org. Chem. 2003, 68, 2812.
(c) Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347. (d) Singh,
R.; Kissling, R. M.; Letellier, M.-A.; Nolan, S. P. J. Org. Chem. 2004, 69,
209.
†
Shanghai Institute of Organic Chemistry.
Institute of Chemical Defense.
Shanghai University.
‡
§
(
1) Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc.
991, 113, 361.
2) For recent reviews on NHCs, see: (a) Enders, D.; Balensiefer, T.
1
(
Acc. Chem. Res. 2004, 37, 534. (b) Nair, V.; Bindu, S.; Sreekumar, V.
Angew. Chem., Int. Ed. 2004, 43, 5130. (c) C e´ sar, V.; Bellemin-Laponnaz,
S.; Gade, L. H. Chem. Soc. ReV. 2004, 33, 619. (d) Herrmann, W. A. Angew.
Chem., Int. Ed. 2002, 41, 1290.
(3) For selected examples, see: (a) Knight, R. L.; Leeper, F. J. J. Chem.
Soc., Perkin Trans. 1 1998, 1891. (b) Enders, D.; Kallfass, U. Angew. Chem.,
Int. Ed. 2002, 41, 1743. (c) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett.
(6) (a) Nair, V.; Bindu, S.; Sreekumar, V.; Rath, N. P. Org. Lett. 2003,
5, 665. (b) Nair, V.; Sreekumar, V.; Bindu, S.; Suresh, E. Org. Lett. 2005,
7, 2297.
1998, 39, 2925. (d) Linghu, X.; Johnson, J. S. Angew. Chem., Int. Ed. 2003,
42, 2534. (e) Pesch, J.; Harms, K.; Bach, T. Eur. J. Org. Chem. 2004, 2025.
(7) Ma, C.; Yang, Y. Org. Lett. 2005, 7, 1343.
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0.1021/ol051422m CCC: $30.25
© 2005 American Chemical Society
Published on Web 07/29/2005