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Letters in Organic Chemistry

Volumn 6, Issue 5, 2009, Pages 377-380

Asymmetric α-amination of aldehydes and ketones catalyzed by tert-butoxy-l-proline

(5) Ait Youcef, Ramzi a Kalch, Delphine a Moreau, Xavier a Thomassigny, Christine a Greck, Christine a

a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES (France)

Author keywords

Azodicarboxylate; Electrophilic amination; Organocatalysis; Tert butoxyproline; hydrazinoalcohol

Indexed keywords

EID: 69549086592 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017809788681293 Document Type: Article

Times cited : (15)

References (35)

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21
- 69549109226
- 4, filtered, and concentrated under reduced pressure. The residue was suspended in 1 M NaOH (6.5 mL) and stirred until the reaction mixture became homogeneous, that is, for about 4h. The reaction mixture was then cooled to 0 °C and acidified with HCl (1M) (6.5mL)
- 3: C, 57.73; H, 9.15; N, 7.48. Found: C, 57.54; H, 8.94; N, 6.91.

22
- 69549139036
- 4, filtered, and concentrated under reduced pressure
- 3: C, 57.73; H, 9.15; N, 7.48. Found: C, 57.46; H, 8.98; N, 7.63.

23
- 69549143123
- General procedure for the amination step: Dibenzylazodicarboxylate (1 mmol) and catalyst (5 mol% or 10 mol%) in dichloromethane (3 mL) were treated with an aldehyde (1.5 mmol) at 0C or room temperature. The reaction mixture was stirred until the yellow color of the azodicarboxylate had disappeared
- 2 1/2) afforded the alcohols.

24
- 69549136374
- major = 55.31 min
- major = 55.31 min.

25
- 0002924105
- See also:
- Poupardin, O.; Greck, C.; Genêt, J.P. Synlett, 1998, 1279. See also:
- (1998) Synlett , pp. 1279
- Poupardin, O.¹ Greck, C.² Genêt, J.P.³

26
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27
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28
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- Poupardin, O.¹ Greck, C.² Genêt, J.P.³

29
- 69549109227
- 22 = - 12.3 (c 1; MeOH)
- 22 = - 12.3 (c 1; MeOH).

30
- 69549136373
- major = 37.90 min
- major = 37.90 min.

31
- 69549083788
- major = 42.30 min
- major = 42.30 min.

32
- 69549115477
- major = 53.28 min
- major = 53.28 min.

33
- 69549131703
- major = 50.03 min
- major = 50.03 min.

34
- 69549085578
- major = 48.37 min
- major = 48.37 min.

35
- 69549137273
- major = 80.11 min
- major = 80.11 min.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.