SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 122, Issue 40, 2000, Pages 9852-9853

Iridium-chiral diphosphine complex catalyzed highly enantioselective pauson-khand-type reaction [9]

(2) Shibata, T a Takagi, K a

a OKAYAMA UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM; METAL COMPLEX; PHOSPHINE DERIVATIVE;

CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; LETTER; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 0034638410 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja000899k Document Type: Letter

Times cited : (198)

References (39)

1
- 0001136410
- Comprehensive Organometallic Chemistry I.I., Hegedus L.S.,Ed. Pergamon Oxford
- (1995) , vol.12 , pp. 703
- Schore, N.E.¹

2
- 0031971911
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 911
- Geis, O.¹ Schmalz, H.-G.²

3
- 0000213863
- Transition Metals In Organic Synthsis; Beller M., Bolm C., Eds., Wiley-VCH, Weinheim
- (1998) , vol.1 , pp. 560
- Jeong, N.¹

4
- 0007670264
- Transition Metals in Total Synthesis; Wiley: New York
- (1990) , pp. 259
- Harrington, P.J.¹

5
- 0001069332
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 3159
- Jeong, N.¹ Hwang, S.H.² Lee, Y.³ Chung, Y.K.⁴

6
- 85022624758
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 8793
- Lee, B.Y.¹ Chung, Y.K.² Jeong, N.³ Lee, Y.⁴ Hwang, S.H.⁵

7
- 0029871213
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2285
- Pagenkopf, B.L.¹ Livinghouse, T.²

8
- 0029928539
- (1996) Tetrahedron Lett. , vol.37 , pp. 3145
- Lee, N.Y.¹ Chung, Y.W.²

9
- 0030668118
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 10549
- Jeong, N.¹ Hwang, S.H.² Lee, Y.K.³ Lim, J.S.⁴

10
- 0031936070
- (1998) Synthesis , pp. 142
- Kim, J.W.¹ Chung, Y.K.²

11
- 0032532517
- (1998) Tetrahedron Lett. , vol.39 , pp. 7637
- Belanger, D.B.¹ O'Mahony, D.J.R.² Livinghouse, T.³

12
- 0032532236
- (1998) Tetrahedron Lett. , vol.39 , pp. 7641
- Belanger, D.B.¹ Livinghouse, T.²

13
- 0032556207
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 10782
- Sugihara, T.¹ Yamaguchi, M.²

14
- 0007684221
- (1998) Synlett , vol.1384
- Sugihara, T.¹ Yamaguchi, M.²

15
- 0034603010
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 631
- Hayashi, M.¹ Hashimoto, Y.² Yamamoto, Y.³ Usuki, J.⁴ Saigo, K.⁵

16
- 0029952824
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9450
- Hicks, F.A.¹ Kablaoui, N.M.² Buchwald, S.L.³

17
- 0033618120
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5881
- Hicks, F.A.¹ Kablaoui, N.M.² Buchwald, S.L.³

18
- 0000687565
- (1997) J. Org. Chem. , vol.62 , pp. 3762
- Morimoto, T.¹ Chatani, N.² Fukumoto, Y.³ Murai, S.⁴

19
- 0030746742
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 6187
- Kondo, T.¹ Suzuki, N.² Okada, T.³ Mitsudo, T.⁴

20
- 0007595962
- (1998) Chem. Lett. , vol.249
- Koga, Y.¹ Kobayashi, T.² Narasaka, K.³

21
- 0001171594
- (1998) Organometallics , vol.17 , pp. 3642
- Jeong, N.¹ Lee, S.² Sung, B.K.³

22
- 0001313544
- (1988) J. Organomet. Chem. , vol.355 , pp. 449
- Bladon, P.¹ Pauson, P.L.² Brunner, H.³ Eder, R.⁴

23
- 0000682825
- (1995) Organometallics , vol.14 , pp. 4986
- Hay, A.M.¹ Kerr, W.J.² Kirk, G.G.³ Milddlemiss, D.⁴

24
- 0007638510
- (1995) Synlett , vol.1085
- Kerr, W.J.¹ Kirk, G.G.² Milddlemiss, D.³

25
- 0000058776
- (1998) Org. Prep. Proced. Int. , vol.30 , pp. 121
- Ingate, S.T.¹ Marco-Contelles, J.²

26
- 0001216151
- Comprehensive Asymmetric Catalysis F.A.; Jacobsen E.N., Pfaltz A., Yamamoto H. Springer Berlin
- (1999) , vol.2 , pp. 491
- Buchwald, S.L.¹ Hicks, F.A.²

27
- 0029909515
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 11688
- Hicks, F.A.¹ Buchwald, S.L.²

28
- 0033523215
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 7026
- Hicks, F.A.¹ Buchwald, S.L.²

29
- 0033597871
- (1999) J. Org. Chem. , vol.64 , pp. 5547
- Sturla, S.J.¹ Buchwald, S.L.²

30
- 0034606977
- During the preparation of this manuscript, an asymmetric catalytic Pauson-Khand reaction was reported but ee is dependent on substituents in enynes and yield is moderate
- (2000) Tetrahedron Lett. , vol.41 , pp. 891
- Hiroi, K.¹ Watanabe, T.² Kawagishi, R.³ Abe, I.⁴

31
- 0343953463
- During the review process of this manuscript, a Rhodium-catalyzed enantioselective intramolecular Pauson-Khand-type reaction was reported
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 6771
- Jeong, N.¹ Sung, B.K.² Choi, Y.K.³

32
- 0007596302
- Rh, which is a very reactive catalyst for the Pauson-Khand-type reaction without phosphine additive (ref 6a), was used in place of Ir under the same conditions ([Rh(COD)Cl]- -tolBINAP, toluene, reflux 36h). But both yield and ee were drastitically decreased (2 (14%, 47% ee), enyne 1 (72% recovered))

33
- 0007684224
- Typical experimental procedure (Table 1, Entry 4): Stirring of tolBINAP (34.3 mg, 0.051 mmol) and [Ir(COD)Cl] (16.3 mg, 0.024 mmol) in toluene (4 mL) at 40 °C under atmospheric pressure of carbon monoxide gave a light yellow solution. After addition of a toluene solution (4 mL) of enyne 1 (83.8 mg, 0.487 mmol), the reaction mixture was refluxed for 24 h. The resulting solution was passed through a small pad of silica gel using a mixed eluent of hexane and ethyl acetate (3/1, v/v). Purification of the crude products by thin-layer chromatography of silica gel afforded pure bicyclic enone 2 (72.7 mg, 0.363 mmol, 75% yield). Ee was determined to be 91% by HPLC analysis using a chiral column

34
- 0007681277
- Enynes possessing 1,2-disubstiuted alkene (for example, diethyl transand cis-1-phenyl-6-octen-1-yne-4,4-dicarboxylate) are not substrates under the same conditions. At this stage, the present asymmetric catalysis by the iridium-to BINAP system has the same synthetic limitation as that by the titanium-EBTHI system (ref 9b)

35
- 0001457964
- The carbonyl insertion between metal and sp-carbon was ascertained by characterization of the acyl metal intermediate in iron carbonyl complex-mediated carbonylative allene-alkyne coupling
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 911
- Shibata, T.¹ Koga, Y.² Narasaka, K.³

36
- 0007672149
- In the Ir-tolBINAP system, the substituent on alkyne might play one of the key roles in high enantioselectivity. In fact enynes possessing terminal alkyne (for example, N-allyl-N-(1,1-dimethyl-2-propynyl)benzylamine) were also catalyzed but in low ee (<20%). On the contrary, in the Co(CO)- -BINAP system, only terminal alkynes show high enantioselectivity to give bicyclic enones in the R form, which is opposite the enantioface selectivity for the Ir-tolBINAP system (ref 10). These results suggest that enantioselectivity is induced by the different mechanism between iridium and cobalt systems

37
- 0000172128
- Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
- (1999) , vol.1 , pp. 199
- Ohkuma, T.¹ Noyori, R.²

38
- 0000696874
- Comprehensive Asymmetric Catalysis, Jacobsen E.N., Pfaltz A., Yamamoto H. Springer Berlin
- (1999) , vol.1 , pp. 247
- Blaser, H.-U.¹ Spindler, F.²

39
- 0002596809
- (1998) J. Org. Chem. , vol.63 , pp. 4
- Murakami, M.¹ Itami, K.² Ubukata, M.³ Tsuji, I.⁴ Ito, Y.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.