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Organic Letters

Volumn 10, Issue 13, 2008, Pages 2781-2783

Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an α-chloroimine

(3) Hodgson, David M a Kloesges, Johannes a Evans, Brian a,b

a UNIVERSITY OF OXFORD (United Kingdom)

b GLAXOSMITHKLINE (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CHLOROIMINE; ALPHA-CHLOROIMINE; AZIRIDINE DERIVATIVE; CERIUM; CHLORINATED HYDROCARBON; IMINE; ORGANIC COMPOUND; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AZIRIDINES; CERIUM; HYDROCARBONS, CHLORINATED; IMINES; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; OXIDATION-REDUCTION; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 51649107330 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol800961a Document Type: Article

Times cited : (37)

References (37)

1
- 1542375289
- (a) Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
- (2004) Tetrahedron , vol.60 , pp. 2701-2743
- Hu, X.E.¹

2
- 77951231590
- Yudin, A. K, Ed, Wiley-VCH: Weinheim
- (b) Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006.
- (2006) Aziridines and Epoxides in Organic Synthesis

3
- 84906433763
- Padwa, A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, 1, pp 1-104.
- (c) Padwa, A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, Vol. 1, pp 1-104.

4
- 18244376859
- (a) Hodgson, D. M.; Humphreys, P. G.; Ward, J. G. Org. Lett. 2005, 7, 1153-1156.
- (2005) Org. Lett , vol.7 , pp. 1153-1156
- Hodgson, D.M.¹ Humphreys, P.G.² Ward, J.G.³

5
- 32044436336
- (b) Hodgson, D. M.; Miles, S. M. Angew. Chem., Int. Ed. 2006, 45, 935-938.
- (2006) Angew. Chem., Int. Ed , vol.45 , pp. 935-938
- Hodgson, D.M.¹ Miles, S.M.²

6
- 33644950248
- (c) Hodgson, D. M.; Humphreys, P. G.; Ward, J. G. Org. Lett. 2006, 8, 995-998.
- (2006) Org. Lett , vol.8 , pp. 995-998
- Hodgson, D.M.¹ Humphreys, P.G.² Ward, J.G.³

7
- 37549039127
- (d) Hodgson, D. M.; Humphreys, P. G.; Miles, S. M.; Brierley, C. A. J.; Ward, J. G. J. Org. Chem. 2007, 72, 10009-10021.
- (2007) J. Org. Chem , vol.72 , pp. 10009-10021
- Hodgson, D.M.¹ Humphreys, P.G.² Miles, S.M.³ Brierley, C.A.J.⁴ Ward, J.G.⁵

8
- 59949085944
- For recent reviews, see: e
- For recent reviews, see: (e) Hodgson, D. M.; Bray, C. D.; Humphreys, P. G. Synlett 2006, 1, 22.
- (2006) Synlett , vol.1 , pp. 22
- Hodgson, D.M.¹ Bray, C.D.² Humphreys, P.G.³

9
- 33846925900
- (f) Hodgson, D. M.; Humphreys, P. G.; Hughes, S. P. Pure Appl. Chem. 2007, 79, 269-280.
- (2007) Pure Appl. Chem , vol.79 , pp. 269-280
- Hodgson, D.M.¹ Humphreys, P.G.² Hughes, S.P.³

10
- 33947226642
- Kawabata, H.; Omura, K.; Uchida, T.; Katsuki, T. Chem. Asian J. 2007, 2, 248-256.
- (2007) Chem. Asian J , vol.2 , pp. 248-256
- Kawabata, H.¹ Omura, K.² Uchida, T.³ Katsuki, T.⁴

11
- 59949097004
- (a) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Synlett 2003, 1985, 1988.
- (1988) Synlett , vol.2003 , pp. 1985
- Morton, D.¹ Pearson, D.² Field, R.A.³ Stockman, R.A.⁴

12
- 33747113614
- For a recent review on chiral nonracemic sulfinimines, see
- (b) For a recent review on chiral nonracemic sulfinimines, see: Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869-8905.
- (2006) Tetrahedron , vol.62 , pp. 8869-8905
- Morton, D.¹ Stockman, R.A.²

13
- 4544268904
- For efficient resolution-based approaches to terminal aziridines from epoxides, see: a
- For efficient resolution-based approaches to terminal aziridines from epoxides, see: (a) Kim, S. K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2004, 43, 3952-3954.
- (2004) Angew. Chem., Int. Ed , vol.43 , pp. 3952-3954
- Kim, S.K.¹ Jacobsen, E.N.²

14
- 8744264856
- (b) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2004, 6, 3973-3975.
- (2004) Org. Lett , vol.6 , pp. 3973-3975
- Bartoli, G.¹ Bosco, M.² Carlone, A.³ Locatelli, M.⁴ Melchiorre, P.⁵ Sambri, L.⁶

15
- 38849191173
- For a recent approach to terminal aziridines, see
- For a recent approach to terminal aziridines, see: Jamookeeah, C. E.; Beadle, C. D.; Jackson, R. F. W.; Harrity, J. P. A. J. Org. Chem. 2008, 73, 1128-1130.
- (2008) J. Org. Chem , vol.73 , pp. 1128-1130
- Jamookeeah, C.E.¹ Beadle, C.D.² Jackson, R.F.W.³ Harrity, J.P.A.⁴

16
- 33746596142
- Denolf, B.; Mangelinckx, S.; Törnroos, K. W.; De Kimpe, N. Org. Lett. 2006, 8, 3129-3132.
- (2006) Org. Lett , vol.8 , pp. 3129-3132
- Denolf, B.¹ Mangelinckx, S.² Törnroos, K.W.³ De Kimpe, N.⁴

17
- 67650015795
- Prepared in one-step from commercially available 4-chloro-1,3-dioxolan-2- one, see:Gross, H.; Costisella, B. Org. Prep. Proced. Int. 1969, 1, 97-98.
- Prepared in one-step from commercially available 4-chloro-1,3-dioxolan-2- one, see:Gross, H.; Costisella, B. Org. Prep. Proced. Int. 1969, 1, 97-98.

18
- 0033575410
- (a) Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883-8904.
- (1999) Tetrahedron , vol.55 , pp. 8883-8904
- Cogan, D.A.¹ Liu, G.² Ellman, J.³

19
- 0036851670
- (b) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
- (2002) Acc. Chem. Res , vol.35 , pp. 984-995
- Ellman, J.A.¹ Owens, T.D.² Tang, T.P.³

20
- 33846463792
- During the course of our work, an isolated example of addition of a Grignard reagent to imine 5 (mesitylMgBr, toluene, -78°C) was reported to give a single diastereomer of the corresponding chlorosulfinamide; this might be attributable to steric effects with this particular reagent, see: Crimmins, M. T.; Shamszad, M. Org. Lett. 2007, 9, 149-152.
- During the course of our work, an isolated example of addition of a Grignard reagent to imine 5 (mesitylMgBr, toluene, -78°C) was reported to give a single diastereomer of the corresponding chlorosulfinamide; this might be attributable to steric effects with this particular reagent, see: Crimmins, M. T.; Shamszad, M. Org. Lett. 2007, 9, 149-152.

21
- 33845282849
- (a) Denmark, S. E.; Weber, T.; Piotrowski, D. W. J. Am. Chem. Soc. 1987, 109, 2223-2225.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 2223-2225
- Denmark, S.E.¹ Weber, T.² Piotrowski, D.W.³

22
- 0033605830
- For a review on organocerium reagents, see
- (b) For a review on organocerium reagents, see: Liu, H.-J.; Shia, K.-S.; Shang, X.; Zhu, B.-Y. Tetrahedron 1999, 55, 3803-3830.
- (1999) Tetrahedron , vol.55 , pp. 3803-3830
- Liu, H.-J.¹ Shia, K.-S.² Shang, X.³ Zhu, B.-Y.⁴

23
- 84985052504
- Mukhopadhyay, T.; Seebach, D. Helv. Chim. Acta 1982, 65, 385-391.
- (1982) Helv. Chim. Acta , vol.65 , pp. 385-391
- Mukhopadhyay, T.¹ Seebach, D.²

24
- 59949091439
- General Procedure. The organolithium (1.2 mmol) in THF (5 mL) was added dropwise to a stirred slurry of CeCl3 (295 mg, 1.2 mmol) in THF (7 mL) at -78°C under argon. After 45 min DMPU (1.5 mL) was added, followed after 15 min by a solution of imine 5 (181 mg, 1 mmol) in THF (3 mL) and the reaction mixture was then allowed to warm to room temperature overnight. Saturated aq NH4Cl (10 mL) and Et2O (5 mL) were added, the reaction mixture filtered through a pad of Celite, and the filter cake washed thoroughly with Et2O (3 x 10 mL, The combined organic layers were washed with H2O (2 x 15 mL) and brine (15 mL, dried (MgSO 4) and evaporated under reduced pressure. Purification of the residue by column chromatography (SiO2, petroleum ether/Et2O) gave the corresponding aziridine 7
- 2O) gave the corresponding aziridine 7.

25
- 59949093978
- 9 to 96:4 (75% yield).
- 9 to 96:4 (75% yield).

26
- 59949100665
- For details, see Supporting Information
- For details, see Supporting Information.

27
- 8144227335
- (a) Hodgson, D. M.; Štefane, B.; Miles, T. J.; Witherington, J. Chem. Commun. 2004, 2234-2235.
- (2004) Chem. Commun , pp. 2234-2235
- Hodgson, D.M.¹ Štefane, B.² Miles, T.J.³ Witherington, J.⁴

28
- 33750464104
- (b) Hodgson, D. M.; Štefane, B.; Miles, T. J.; Witherington, J. J. Org. Chem. 2006, 71, 8510-8515.
- (2006) J. Org. Chem , vol.71 , pp. 8510-8515
- Hodgson, D.M.¹ Štefane, B.² Miles, T.J.³ Witherington, J.⁴

29
- 33747596469
- (c) Hanessian, S.; Del Valle, J. R.; Xue, Y.; Blomberg, N. J. Am. Chem. Soc. 2006, 128, 10491-10495.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 10491-10495
- Hanessian, S.¹ Del Valle, J.R.² Xue, Y.³ Blomberg, N.⁴

30
- 3242726231
- (a) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377-2380.
- (2004) Org. Lett , vol.6 , pp. 2377-2380
- Morton, D.¹ Pearson, D.² Field, R.A.³ Stockman, R.A.⁴

31
- 9344259155
- (b) Chemla, F.; Ferreira, F. J. Org. Chem. 2004, 69, 8244-3250.
- (2004) J. Org. Chem , vol.69 , pp. 8244-3250
- Chemla, F.¹ Ferreira, F.²

32
- 34247645401
- (c) Denolf, B.; Leemans, E.; De Kimpe, N. J. Org. Chem. 2007, 72, 3211-3217.
- (2007) J. Org. Chem , vol.72 , pp. 3211-3217
- Denolf, B.¹ Leemans, E.² De Kimpe, N.³

33
- 34250624070
- (d) Kokotos, C. G.; Aggarwal, V. K. Org. Lett. 2007, 9, 2099-2102.
- (2007) Org. Lett , vol.9 , pp. 2099-2102
- Kokotos, C.G.¹ Aggarwal, V.K.²

34
- 59949088853
- The principal authors of refs 17a,c and d have accepted that their published data for material obtained on deprotection are not consistent with that expected for the deprotected aziridines (personal communications with Profs. Stockman, De Kimpe, and Aggarwal).
- The principal authors of refs 17a,c and d have accepted that their published data for material obtained on deprotection are not consistent with that expected for the deprotected aziridines (personal communications with Profs. Stockman, De Kimpe, and Aggarwal).

35
- 0001043464
- (a) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404-5406.
- (1990) J. Org. Chem , vol.55 , pp. 5404-5406
- Bailey, W.F.¹ Punzalan, E.R.²

36
- 0001013027
- (b) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406-5409.
- (1990) J. Org. Chem , vol.55 , pp. 5406-5409
- Negishi, E.¹ Swanson, D.R.² Rousset, C.J.³

37
- 0027200444
- Guertin, K. R.; Kende, A. S. Tetrahedron Lett. 1993, 34, 5369-5372.
- (1993) Tetrahedron Lett , vol.34 , pp. 5369-5372
- Guertin, K.R.¹ Kende, A.S.²

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