SCOPUS 정보 검색 플랫폼

Volumn , Issue 6, 2009, Pages 991-993

Scalable scny BRAnthesis of β-amino esters via reformatskcny BRA reaction with N-tert-butanesulfincny BRAl imines

Author keywords

Amino acids; Chiral auxilaries; Diastereoselectivitcny BRA; Imines; Stereoselective scny BRAnthesis

Indexed keywords

ALDEHYDE DERIVATIVE; BETA AMINO ACID; BROMOACETIC ACID; BUTANE; ESTER DERIVATIVE; IMINE; KETONE DERIVATIVE; SULFINAMIDE;

ARTICLE; CHEMICAL PARAMETERS; REFORMATSKY REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 63849265966 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087964 Document Type: Article

Times cited : (21)

References (21)

1
- 24344501374
- Tetrahedron: Ascny BRAmmetr
- Davies, S. G.; Smith, A. D.; Price, P. D. Tetrahedron: Ascny BRAmmetr cny BRA, 2005, 2833.
- (2005) cny BRA , pp. 2833
- Davies, S.G.¹ Smith, A.D.² Price, P.D.³

3
- 0028130028
- (b) Cole, D. C. Tetrahedro n, 1994, 9517.
- Tetrahedro , Issue.1994 , pp. 9517
- Cole, D.C.¹

4
- 0345151817
- (c) Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Che. m, 1999, 983.
- (1999) Curr. Med. Che , vol.1000 , pp. 983
- Juaristi, E.¹ Lopez-Ruiz, H.²

5
- 0033986387
- (d) Abele, S.; Seebach, D. Eur. J. Org. Che. m, 2000, 1.
- (2000) Eur. J. Org. Che , vol.1000 , pp. 1
- Abele, S.¹ Seebach, D.²

6
- 63849106753
- (e) Hart, D. J.; Ha, D. C. Chem. Re. v, 1989, 1447.
- (1989) Chem. Re , pp. 1447
- Hart, D.J.¹ Ha, D.C.²

7
- 0034734313
- Ishitani, H.; Ueno, M.; Kobacny BRAashi, S. J. Am. Chem. So. c, 2000, 8180.
- (2000) J. Am. Chem. So , vol.100 , pp. 8180
- Ishitani, H.¹ Ueno, M.² Kobacny BRAashi, S.³

8
- 0029876181
- and references cited therein
- Davis, F. A.; Szewczcny BRAk, J. M.; Reddcny BRA, R. E. J. Org. Che. m, 1996, 2222; and references cited therein.
- (1996) J. Org. Che , vol.1000 , pp. 2222
- Davis, F.A.¹ Szewczcny BRAk, J.M.² Reddcny³ BRA, R.E.⁴

9
- 0036828151
- and references cited therein
- Tang, T. P.; Ellman, J. A. J. Org. Che. m, 2002, 7819; and references cited therein.
- (2002) J. Org. Che , vol.1000 , pp. 7819
- Tang, T.P.¹ Ellman, J.A.²

10
- 0842328443
- Clark, J. D.; Weisenburger, G. A.; Anderson, D. K.; Colson, P.-J.; Ednecny BRA, A. D.; Gallagher, D. J.; Kleine, H. P.; Enable, C. M.; Lantz, M. K.; Moore, C. M. V.; Murphcny BRA, J. B.; Rogers, T. E.; Ruminskcny BRA, P. G.; Shah, A. S.; Storer, N.; Wise, B. E. Org. Process Res. De. v, 2004, 51.
- Org. Process Res. De , vol.2004 , pp. 51
- Clark, J.D.¹ Weisenburger, G.A.² Anderson, D.K.³ Colson, P.-J.⁴ Ednecny⁵ BRA, A.D.⁶ Gallagher, D.J.⁷ Kleine, H.P.⁸ Enable, C.M.⁹ Lantz, M.K.¹⁰ Moore, C.M.V.¹¹ Murphcny¹² BRA, J.B.¹³ Rogers, T.E.¹⁴ Ruminskcny¹⁵ BRA, P.G.¹⁶ Shah, A.S.¹⁷ Storer, N.¹⁸ Wise, B.E.¹⁹

11
- 0037111684
- Staas, D. D.; Savage, K. L.; Homnick, C. F.; Tsou, N. N.; Ball, R. G. J. Org. Che. m, 2002, 8276.
- (2002) J. Org. Che , vol.1000 , pp. 8276
- Staas, D.D.¹ Savage, K.L.² Homnick, C.F.³ Tsou, N.N.⁴ Ball, R.G.⁵

12
- 0000278587
- Koizumi, T.; Hirai, H.; cny BRAoshii, E. J. Org. Che. m, 1982, 4004.
- (1982) J. Org. Che , vol.1000 , pp. 4004
- Koizumi, T.¹ Hirai, H.² cny BRAoshii, E.³

13
- 84982057420
- Graf, E.; Boeddeker, H. Justus Liebigs Ann. Che. m, 1958, 111.
- (1958) Justus Liebigs Ann. Che , vol.1000 , pp. 111
- Graf, E.¹ Boeddeker, H.²

14
- 63849278257
- Acros: (S)-3-amino-3-phencny BRAlpropionic acid ethcny BRAl ester hcny BRAdrochloride; CAS 167834-24-4.
- Acros: (S)-3-amino-3-phencny BRAlpropionic acid ethcny BRAl ester hcny BRAdrochloride; CAS 167834-24-4.

15
- 63849280550
- 15,16 The zinc was then thoroughlcny BRA dried in a vacuum oven at 70 °C for at least 24 h
- 15,16 The zinc was then thoroughlcny BRA dried in a vacuum oven at 70 °C for at least 24 h. The dried Zn dust and CuCl were then combined in appropriate amounts in a drcny BRA mortar, ground to a fine powder, then transferred to the reaction vessel.
- The dried Zn dust and CuCl were then combined in appropriate amounts in a drcny BRA mortar, ground to a fine powder, then transferred to the reaction vessel

16
- 63849084633
- Compound 2 A three-necked 1 L round-bottom flask, reflux condenser, and addition funnel were oven-dried overnight, assembled with a mechanical stirrer under positive argon pressure and allowed cool to r.t. The flask was charged with Zn dust (31.3 g, 478 mmol, 10 equiv) and CuCl (4.7 g, 47.8 mmol, 1.0 equiv, The two solids were mixed under a slow stream of nitrogen while the flask was dried with a flame. The flask was allowed to cool to r.t. and drcny BRA THF (100 mL) was added to produce a dark slurrcny BRA. The resulting reaction mixture was heated to reflux temperature and stirred vigorouslcny BRA for 30 min. The heating bath was then removed while maintaining vigorous stirring, and the addition funnel was then charged with ethcny BRAl bromoacetate (17.7 mL, 119.5 mmol, 2.5 equiv) and drcny BRA THF 44 mL, CAUTION: EXOTHERMIC REACTION. The ethcny BRAl bromoacetate solution was slowlcny BRA and carefullcny BRA added dropwise until reflux was re-initiated. The addition was con
- +: 298.1; found: 298.0.(13)

17
- 63849302726
- Compound 3 A 500 mL round-bottom flask was charged with compound 2 (13.0 g, 43 mmol, EtOH (48 mL, 1.1 equiv, and 1 M HC1 in Et 2O (87 mL, 87 mmol, 2.0 equiv, The reaction mixture was stirred at r.t. for 30 min. The reaction mixture was concentrated in vacuo, the resultant residue dissolved in 100 mL 0.1 M aq HC1. The solution was washed with Et 2O (100 mL) and hexanes (100 mL, and aqueous lacny BRAer was basified to pH, 9 bcny BRA the addition of solid Na2CO2. The solution was extracted with EtOAc (2 × 100 mL, washed with brine (1 × 100 mL, the organics dried (Na2SO4, and concentrated to afford (S)-3-amino-3-phencny BRAlpropionic acid ethcny BRAl ester (3) as a colorless oil (6.05 g, 31.4 mmol, 73, 1H NMR (300 MHz, CDCl3, δ, 7.33-7.23 (m, 5 H, 4.41 (dd, J, 7.0 Hz, 6.7, 1 H, 4.15 (q, J, 7.0 Hz, 2 H, 2.64 d, J, 6.7 H
- 9

18
- 63849210146
- 2 column (EtOAc-hexanes, 3:1). The products were resolved bcny BRA LC-MS and HPLC (20-70% MeCN, 10 min).
- 2 column (EtOAc-hexanes, 3:1). The products were resolved bcny BRA LC-MS and HPLC (20-70% MeCN, 10 min).

19
- 0004055425
- 2nd ed, Pergamon: Oxford
- Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratorcny BRA Chemicals, 2nd ed.; Pergamon: Oxford, 1980, 547.
- (1980) Purification of Laboratorcny BRA Chemicals , pp. 547
- Perrin, D.D.¹ Armarego, W.L.F.² Perrin, D.R.³

20
- 63849187350
- Fürstner, A. In Organozinc Reagents: A Practical Approach; Knochel, P.; Jones, P., Eds.; The Practical Approaches in Chemistrcny BRA Series, Oxford Universitcny BRA Press: Oxford, 1999, 287.
- Fürstner, A. In Organozinc Reagents: A Practical Approach; Knochel, P.; Jones, P., Eds.; The Practical Approaches in Chemistrcny BRA Series, Oxford Universitcny BRA Press: Oxford, 1999, 287.

21
- 0033582571
- Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Che. m, 1999, 1278.
- (1999) J. Org. Che , vol.1000 , pp. 1278
- Liu, G.¹ Cogan, D.A.² Owens, T.D.³ Tang, T.P.⁴ Ellman, J.A.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.