References and Notes
1a
Atkins GM.
Burgess EM.
J. Am. Chem. Soc.
1968,
90:
4744
1b
Burgess EM.
Penton HR.
Taylor EA.
J. Am. Chem. Soc.
1970,
92:
5224
1c
Atkins GM.
Burgess EM.
J. Am. Chem. Soc.
1972,
94:
6135
1d
Burgess EM.
Penton HR.
Taylor EA.
J. Org. Chem.
1973,
38:
26
For reviews of Burgess Reagent see:
2a
Burckhardt S.
Synlett
2000,
559
2b
Lamberth C.
J. Prakt. Chem.
2000,
342:
518
2c
Taibe P.
Mobashery S. In Encyclopedia of Reagents in Organic Synthesis
Vol. 5:
Paquette LA.
Wiley;
Chichester:
1995.
p.3345
2d
Khapli S.
Dey S.
Mal D.
J. Ind. Inst. Sci.
2001,
81:
461
3 The following statement appeared in a review by Lamberth (ref. 2b) published in 2000: ‘The compatibility of the Burgess reagent with many functionalities, e.g. halogens, epoxides, alkenes, alkynes, aldehydes, ketones, acetals, esters, secondary amides, makes it an attractive technique for the introduction of C-C double bonds into highly functionalized molecules.’
4
Rinner U.
Adams DR.
dos Santos ML.
Abboud KA.
Hudlicky T.
Synlett
2003,
1247
5a
Nicolaou KC.
Snyder SA.
Nalbandian AZ.
Longbottom DA.
J. Am. Chem. Soc.
2004,
126:
6234
5b
Nicolaou KC.
Huang X.
Snyder SA.
Rao PB.
Bella M.
Reddy MV.
Angew. Chem. Int. Ed.
2002,
41:
834
5c
Nicolaou KC.
Snyder SA.
Longbottom DA.
Nalbandian AZ.
Huang X.
Chem. Eur. J.
2004,
10:
5581
5d
Nicolaou KC.
Longbottom DA.
Snyder SA.
Nalbandian AZ.
Huang X.
Angew. Chem. Int. Ed.
2002,
41:
3866
6a
Schneider C.
Sreekanth AR.
Mai E.
Angew. Chem. Int. Ed.
2004,
43:
5691
6b
Yang M.
Zhu C.
Yuan F.
Huang Y.
Pan Y.
Org. Lett.
2005,
7:
1927
6c
Schaus SE.
Larrow JF.
Jacobsen EN.
J. Org. Chem.
1997,
62:
4197
6d
Sagawa S.
Abe H.
Hase Y.
Inaba T.
J. Org. Chem.
1999,
64:
4962
6e
Iida T.
Yamamoto N.
Matsunaga S.
Woo H.-G.
Shibasaki M.
Angew. Chem. Int. Ed.
1998,
37:
2223
6f
Carrée F.
Gil R.
Collin J.
Org. Lett.
2005,
7:
1023
6g
Bartoli G.
Bosco M.
Carlone A.
Locatelli M.
Melchiorre P.
Sembri L.
Org. Lett.
2004,
6:
3973
6h
Bartoli G.
Bosco M.
Carlone A.
Locatelli M.
Massaccesi M.
Melchiorre P.
Sembri L.
Org. Lett.
2004,
6:
2173
6i
Bandini M.
Cozzi PG.
Melchiorre P.
Umani-Ronchi A.
Angew. Chem. Int. Ed.
2004,
43:
84
7
Martinez LE.
Leighton JL.
Carsten DH.
Jacobsen EN.
J. Am. Chem. Soc.
1995,
117:
5897
8
Bolm C.
Ewald M.
Felder M.
Schlingloff G.
Chem. Ber.
1992,
125:
1169
9 We thank Prof. Travis Dudding (Brock University) for performing transition state optimization calculations (Gaussian 03) for the C
2 catalysts as well as for the menthol auxiliary. Full details of these calculations will be disclosed in an upcoming full paper.
10 We thank one of the referees for suggesting this explanation.
For reviews on the synthesis and utility of 1,2-amino-alcohols see:
11a
Shaw G. In Comprehensive Heterocyclic Chemistry II
Katritzky AR.
Rees CW.
Scriven EFV.
Pergamon Press;
New York:
1996.
p.397
11b
Wallbaum S.
Martens J.
Tetrahedron: Asymmetry
1992,
3:
1475
11c
Noyori R.
Kitamura M.
Angew. Chem., Int. Ed. Engl.
1991,
193:
34
11d
Singh VK.
Synthesis
1991,
605
12
de Parrodi CA.
Juaristi E.
Quinterno L.
Clara-Sosa A.
Tetrahedron: Asymmetry
1997,
8:
1075
13
Pelphrey PM.
Abboud KA.
Wright DL.
J. Org. Chem.
2004,
69:
6931
14 Compound 18: colorless oil; [α]D
23 -48.5 (c 0.275, CHCl3). IR (film): ν = 3448, 3340, 2956, 2926, 2871, 1631, 1548, 1496, 1446, 1372, 1322, 1173, 1097, 986, 954, 917, 863, 815, 759, 700, 661, 609, 541 cm-1. 1H NMR (499 MHz, CDCl3): δ = 7.28-7.46 (m, 5 H), 7.06 (br s, 1 H), 5.76 (br s, 1 H), 5.06 (dt, J = 9.3, 2.2 Hz, 1 H), 4.80 (td, J = 11.0, 4.6 Hz, 1 H), 4.24 (ddd, J = 10.6, 8.8, 2.8 Hz, 1 H), 4.13 (ddd, J = 18.2, 10.3, 9.2 Hz, 1 H), 2.68 (br s, 1 H), 2.08 (d, J = 12.5 Hz, 1 H), 1.83-1.91 (m, 1 H), 1.67 (d, J = 12.1 Hz, 2 H), 1.32-1.51 (m, 2 H), 0.99 (q, J = 11.6 Hz, 1 H), 0.91 (d, J = 5.8 Hz, 3 H), 0.89 (dd, J = 6.8, 1.0 Hz, 3 H), 0.85 (m, 1 H), 0.76 (t, J = 6.5 Hz, 3 H). 13C NMR (126 MHz, CDCl3): δ = 160.3, 138.5, 129.1, 128.7, 126.5, 79.5, 75.0, 72.1, 47.1, 40.7, 34.1, 31.5, 26.4, 23.3, 22.4, 21.2, 16.8. HRMS: m/z calcd for C19H30N2O5S: 398.1875; found: 398.1855.
15 We thank Dr. Ion Ghiviriga (NMR) and Dr. David Powell (mass spectrometry) from the University of Florida for their assistance with the structure assignment of 18. The details of these assignments will be reported in an upcoming full paper.
