SCOPUS 정보 검색 플랫폼

Volumn , Issue 13, 2009, Pages 2076-2078

Catalytic decarbonylation of epoxyaldehydes: Applications to the preparation of terminal epoxides

Author keywords

Asymmetric synthesis; Decarbonylation; Epoxides; Homogenous catalysis; Rhodium

Indexed keywords

ALDEHYDE DERIVATIVE; EPOXIDE; RHODIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CARBONYLATION; CHEMICAL BOND; ENANTIOSELECTIVITY; EPOXIDATION;

EID: 68949157431 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217562 Document Type: Article

Times cited : (6)

References (14)

1
- 0001945139
- Ohno, K.; Tsuji, J. J. Am. Chem. Soc. 1969, 90, 99.
- (1969) J. Am. Chem. Soc , vol.90 , pp. 99
- Ohno, K.¹ Tsuji, J.²

2
- 37349031135
- Int. Ed
- Fessard, T.; Andrews, S. P.; Motoyoshi, H.; Carreira, E. M. Ang. Chem. Int. Ed. 2007, 46, 9331.
- (2007) Ang. Chem , vol.46 , pp. 9331
- Fessard, T.¹ Andrews, S.P.² Motoyoshi, H.³ Carreira, E.M.⁴

3
- 36849039996
- Monrad, R. N.; Madsen, R. J. Org. Chem. 2007, 72, 9782.
- (2007) J. Org. Chem , vol.72 , pp. 9782
- Monrad, R.N.¹ Madsen, R.²

4
- 85082943077
- For a review, see
- For a review, see: Pfenninger, A. Synthesis 1986, 89.
- (1986) Synthesis , pp. 89
- Pfenninger, A.¹

5
- 0037138704
- Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 1307
- Schaus, S.E.¹ Brandes, B.D.² Larrow, J.F.³ Tokunaga, M.⁴ Hansen, K.B.⁵ Gould, A.E.⁶ Furrow, M.E.⁷ Jacobsen, E.N.⁸

6
- 6044269452
- For a general review on organocatalysis, see
- For a general review on organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5138
- Dalko, P.I.¹ Moisan, L.²

7
- 18744407280
- Marigo, M.; Franzen, J.; Poulsen, T. B.; Zhuang, W.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 6964
- Marigo, M.¹ Franzen, J.² Poulsen, T.B.³ Zhuang, W.⁴ Jorgensen, K.A.⁵

8
- 0030665236
- Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 11224
- Wang, Z.-X.¹ Tu, Y.² Frohn, M.³ Zhang, J.-R.⁴ Shi, Y.⁵

9
- 38849159178
- Wang, X.; List, B. Angew. Chem. Int. Ed. 2007, 47, 1119.
- (2007) Angew. Chem. Int. Ed , vol.47 , pp. 1119
- Wang, X.¹ List, B.²

10
- 48749097850
- Sone, T.; Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 10078.
- (2008) J. Am. Chem. Soc , vol.130 , pp. 10078
- Sone, T.¹ Yamaguchi, A.² Matsunaga, S.³ Shibasaki, M.⁴

11
- 33749245879
- Arends, I. W. C. E. Angew. Chem. Int. Ed. 2006, 45, 6250.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6250
- Arends, I.W.C.E.¹

12
- 0000483875
- For more information on rhodaoxetane, see
- For more information on rhodaoxetane, see: Calhorda, M. J.; Galvao, A. M.; Uenaleroglu, C.; Zlota, A.; Frolow, F.; Milstein, D. Organometallics 1993, 12, 3316.
- (1993) Organometallics , vol.12 , pp. 3316
- Calhorda, M.J.¹ Galvao, A.M.² Uenaleroglu, C.³ Zlota, A.⁴ Frolow, F.⁵ Milstein, D.⁶

13
- 68949085998
- General procedure for the decarbonylation reaction: [Rh(cod)Cl]2 (3.8 mg, 0.0077 mmol) and rac-BINAP (18.5 mg, 0.03 mmol) were dissolved in o-dichlorobenzene (3 mL) in a 25 mL sealed tube under an argon atmosphere. After 15 min of stirring at r.t, a homogenous dark-red solution formed. The corresponding α,β-epoxyaldehyde (0.3 mmol) was then added to the stirring mixture, the tube was evacuated and filled with argon three times and finally sealed under vacuum. The reaction mixture was then immerged in a pre-heated oil bath at the corresponding temperature (140 °C, After 14 h, the mixture was cooled to r.t. and directly loaded onto a column packed with silica gel. Prior elution with pure pentane to remove the o-dichlorobenzene, followed by elution with the corresponding solvent mixture (pentane-Et2O) afforded the pure compound as an oil. Caution: careful work-up is necessary since some of the products are highly volatile! Triisop
- +: 335.2377; found: 335.2376.

14
- 20844461898
- Nishiguchi, G. A.; Little, R. D. J. Org. Chem. 2005, 70, 5249.
- (2005) J. Org. Chem , vol.70 , pp. 5249
- Nishiguchi, G.A.¹ Little, R.D.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.