Abstract
A facile strategy for enantioselective synthesis of (R)-salmeterol is described via a chiral auxiliary starting from 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanone through four or five steps. The product was obtained in good purity, enantiomeric excess and yield.
Keywords
References
1.
Nials A.T.
,
Coleman R. A.
,
Johnson M.
, and
Sumner M. J.
, J. Am. Rev. Resp. Dis. , 1994 , 149 , A481 .
2.
Jeppsson A.B.
,
Löfdahl C. G.
,
Waldeck B.
, and
Widmark E.
, Pulm. Pharmacol. , 1989 , 2 , 81 .
3.
Adolfsson L.-E.
,
Lundgren M.
,
Tilling B.
,
Jern S.
,
Tyren C.
,
Godwood A.
, and
Gor D.
, Clin. Drug Invest. , 2005 , 25 , 231 .
4.
Bhosale D.S.
,
Drabina P.
,
Kincl M.
,
Vlcek M.
, and
Sedlak M.
, Tetrahedron Asymmetry , 2015 , 26 , 1300 .
5.
Bream R.N.
,
Ley S. V.
,
Mcdermott B.
, and
Procopiou P. A.
, J. Chem. Soc. Perkin Trans. 1 , 2002 , 2237 .
6.
Goswami J.
,
Bezbaruah R. L.
,
Goswami A.
, and
Borthakur N.
, Tetrahedron Asymmetry , 2002 , 12 , 3343 .
7.
Procopiou P.A.
, PCT Int. Appl. WO 2001096278, December 2001 .
8.
Bream R.N.
,
Ley S. V.
, and
Procopiou P. A.
, Org. Lett. , 2002 , 4 , 3793 .
9.
Coe D.M.
,
Perciaccante R.
, and
Procopiou P. A.
, Org. Biomol. Chem. , 2003 , 1 , 1106 .
10.
Hett R.
,
Stare R.
, and
Helquist P.
, Tetrahedron. Lett. , 1994 , 35 , 9375 .
11.
Liu J.
,
Zhou D.
,
Jia X.
,
Huang L.
,
Li X.
, and
Chan A. S. C.
, Tetrahedron Asymmetry , 2008 , 19 , 1824 .
12.
Buchanan D.J.
,
Dixon D. J.
, and
Looker B. E.
, Synlett , 2005 , 12 , 1948 .
13.
Li W.
,
Huang H.
,
Jin X.
,
Liu Y.
,
Xu C.
, and
Zhu H.
, Chem. Res. Chinese Universities , 2014 , 30 , 770 .
14.
Guo Z.-L.
,
Deng Y.-Q.
,
Zhong S.
, and
Lu G.
, Tetrahedron Asymmetry , 2011 , 22 , 1395 .
15.
Liu B.
,
Yin L.
,
Jia X.
, and
Li X.
, Zhongguo Yaowu Huaxue Zazhi , 2009 , 19 , 407 .
16.
Goswami J.
,
Bezbaruah R. L.
,
Goswami A.
, and
Borthakur N.
, Tetrahedron Asymmetry , 2001 , 12 , 3343 .
17.
Panayiotis A.P.
, and
Gillian E. M.
, Tetrahedron Asymmetry , 2001 , 12 , 2005 .
18.
Lunts H.L.
, and
Toon P.
, US patent 3644353, February 1972 .
19.
Quan X.
,
Lin C.-G.
,
Xu J.
, and
Shi H.-J.
, Chin. J. Org. Chem. , 2009 , 29 , 648 .
20.
Rong Y.
, and
Ruoho A. E.
, Synth. Commun. , 1999 , 29 , 2155 .
