SCOPUS 정보 검색 플랫폼

Volumn 13, Issue 20, 2015, Pages 5591-5596

Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: An organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent

(6) Massolo, Elisabetta a Benaglia, Maurizio a Genoni, Andrea a Annunziata, Rita a Celentano, Giuseppe a Gaggero, Nicoletta a

a UNIVERSITY OF MILAN (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

POSITIVE IONS;

ASYMMETRIC ADDITION; CONJUGATE ADDITION; MILD REACTION CONDITIONS; SIMULTANEOUS REDUCTION; STEREO-SELECTIVE; STEREOSELECTIVE ADDITION; STEREOSELECTIVE REACTIONS; SYNTHETIC TRANSFORMATIONS;

STEREOSELECTIVITY;

1,3-DITHIANE; 4 AMINOBUTYRIC ACID B RECEPTOR; 4 AMINOBUTYRIC ACID B RECEPTOR STIMULATING AGENT; ALKENE; ANION; BACLOFEN; GLYOXYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; NITRO DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKENES; ANIONS; BACLOFEN; CATALYSIS; GABA-B RECEPTOR AGONISTS; GLYOXYLATES; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; RECEPTORS, GABA-B; STEREOISOMERISM;

EID: 84929377591 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c5ob00492f Document Type: Article

Times cited : (28)

References (48)

1
- 51049122384
- See also
- M. Shibasaki M. Kanai Chem. Rev. 2008 108 2853
- (2008) Chem. Rev. , vol.108 , pp. 2853
- Shibasaki, M.¹ Kanai, M.²

2
- 34547207611
- Q. Kang Z. A. Zhao S. L. You Adv. Synth. Catal. 2007 349 1657
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1657
- Kang, Q.¹ Zhao, Z.A.² You, S.L.³

3
- 0036462607
- See also
- M. J. Kiefel M. von Itzstein Chem. Rev. 2002 102 471
- (2002) Chem. Rev. , vol.102 , pp. 471
- Kiefel, M.J.¹ Von Itzstein, M.²

4
- 0003433653
- Pergamon Press, New York, ch. 2
- S. Hanessian, Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, New York, 1983, ch. 2
- (1983) Total Synthesis of Natural Products: The Chiron Approach
- Hanessian, S.¹

5
- 79955596607
- See also
- K. M. Steward J. S. Johnson Org. Lett. 2011 13 2426
- (2011) Org. Lett. , vol.13 , pp. 2426
- Steward, K.M.¹ Johnson, J.S.²

6
- 84866508672
- For a similar approach in the synthesis of chiral ketones through catalytic oxidative C-C bond cleavage of aldehydes by oxygen, see
- M. W. Leighty B. Shen J. N. Johnston J. Am. Chem. Soc. 2012 134 15233
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 15233
- Leighty, M.W.¹ Shen, B.² Johnston, J.N.³

7
- 84863115251
- B. Tiwari J. Zhang Y. R. Chi Angew. Chem., Int. Ed. 2012 51 1911
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 1911
- Tiwari, B.¹ Zhang, J.² Chi, Y.R.³

8
- 0018454939
- For a review on organocatalytic umpolung, see
- D. Seebach Angew. Chem., Int. Ed. 1979 18 239
- (1979) Angew. Chem., Int. Ed. , vol.18 , pp. 239
- Seebach, D.¹

9
- 84859747983
- For some recent papers on organocatalytic additions of acyl anion synthons, see
- X. Bugaut F. Glorius Chem. Soc. Rev. 2012 41 3511
- (2012) Chem. Soc. Rev. , vol.41 , pp. 3511
- Bugaut, X.¹ Glorius, F.²

10
- 45249095786
- T. Hashimoto M. Hirose K. Maruoka J. Am. Chem. Soc. 2008 130 7556
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7556
- Hashimoto, T.¹ Hirose, M.² Maruoka, K.³

11
- 34548153520
- M. Rueping E. Sugiono T. Theissman A. Kuenkel A. Kiickritz A. Pews-Davtyan N. Nemati M. Beller Org. Lett. 2007 1065
- (2007) Org. Lett. , pp. 1065
- Rueping, M.¹ Sugiono, E.² Theissman, T.³ Kuenkel, A.⁴ Kiickritz, A.⁵ Pews-Davtyan, A.⁶ Nemati, N.⁷ Beller, M.⁸

12
- 79956064751
- B. Alonso E. Reyes L. Carillo J. L. Vicario D. Badia Chem.-Eur. J. 2011 17 6048
- (2011) Chem.-Eur. J. , vol.17 , pp. 6048
- Alonso, B.¹ Reyes, E.² Carillo, L.³ Vicario, J.L.⁴ Badia, D.⁵

13
- 84864260031
- M. Fernández U. Uria J. L. Vicario E. Reyes L. Carrillo J. Am. Chem. Soc. 2012 134 11872
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 11872
- Fernández, M.¹ Uria, U.² Vicario, J.L.³ Reyes, E.⁴ Carrillo, L.⁵

14
- 84864643928
- D. Monge A. M. Crespo-Peña E. Martín-Zamora E. Álvarez R. Fernández J. M. Lassaletta J. Am. Chem. Soc. 2012 134 12912
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 12912
- Monge, D.¹ Crespo-Peña, A.M.² Martín-Zamora, E.³ Álvarez, E.⁴ Fernández, R.⁵ Lassaletta, J.M.⁶

15
- 84879158524
- Reviews
- A. M. Crespo-Peña D. Monge E. Martín-Zamora E. Álvarez R. Fernández J. M. Lassaletta Chem.-Eur. J. 2013 19 8421
- (2013) Chem.-Eur. J. , vol.19 , pp. 8421
- Crespo-Peña, A.M.¹ Monge, D.² Martín-Zamora, E.³ Álvarez, E.⁴ Fernández, R.⁵ Lassaletta, J.M.⁶

16
- 38349109278
- D. Enders O. Niemeier A. Henseler Chem. Rev. 2007 107 5606
- (2007) Chem. Rev. , vol.107 , pp. 5606
- Enders, D.¹ Niemeier, O.² Henseler, A.³

17
- 84862577173
- H. U. Vora P. Wheleer T. Rovis Adv. Synth. Catal. 2012 354 1617
- (2012) Adv. Synth. Catal. , vol.354 , pp. 1617
- Vora, H.U.¹ Wheleer, P.² Rovis, T.³

18
- 84859747983
- For more recent contributions, see
- X. Bugaut F. Glorius Chem. Soc. Rev. 2012 41 3511
- (2012) Chem. Soc. Rev. , vol.41 , pp. 3511
- Bugaut, X.¹ Glorius, F.²

19
- 84887850831
- references cited therein
- O. Bortolini G. Fantin V. Ferretti M. Fogagnolo P. P. Giovannini A. Masso S. Pacifico D. Ragno Adv. Synth. Catal. 2013 355 3244
- (2013) Adv. Synth. Catal. , vol.355 , pp. 3244
- Bortolini, O.¹ Fantin, G.² Ferretti, V.³ Fogagnolo, M.⁴ Giovannini, P.P.⁵ Masso, A.⁶ Pacifico, S.⁷ Ragno, D.⁸

20
- 84887946842
- See also the review
- M. M. D. Wilde M. Gravel Angew. Chem., Int. Ed. 2013 52 12651
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 12651
- Wilde, M.M.D.¹ Gravel, M.²

21
- 84875799416
- S. J. Ryan L. Candish D. W. Lupton Chem. Soc. Rev. 2013 42 4906
- (2013) Chem. Soc. Rev. , vol.42 , pp. 4906
- Ryan, S.J.¹ Candish, L.² Lupton, D.W.³

22
- 34250374484
- For a recent contribution, see
- D. Enders M. Bonten G. Raabe Angew. Chem., Int. Ed. 2007 46 2314
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2314
- Enders, D.¹ Bonten, M.² Raabe, G.³

23
- 84887110732
- See also
- K. S. Yang A. E. Nibbs Y. E. Turkmen V. H. Rawal J. Am. Chem. Soc. 2013 135 16050
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 16050
- Yang, K.S.¹ Nibbs, A.E.² Turkmen, Y.E.³ Rawal, V.H.⁴

24
- 84870313461
- limited examples, see
- P. A. Evans S. Oliver J. J. Chae J. Am. Chem. Soc. 2012 134 19314
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 19314
- Evans, P.A.¹ Oliver, S.² Chae, J.J.³

25
- 19044378567
- M. Amat M. Perez N. Llor J. Bosch Org. Lett. 2002 4 2787
- (2002) Org. Lett. , vol.4 , pp. 2787
- Amat, M.¹ Perez, M.² Llor, N.³ Bosch, J.⁴

26
- 0037162667
- I. Coldham K. M. Crapnell J.-C. Fernandez J. D. Moseley R. Rabot J. Org. Chem. 2002 67 6181
- (2002) J. Org. Chem. , vol.67 , pp. 6181
- Coldham, I.¹ Crapnell, K.M.² Fernandez, J.-C.³ Moseley, J.D.⁴ Rabot, R.⁵

27
- 4143144245
- references cited therein For a recent catalytic, non-stereoselective, conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to unsaturated ketones, see
- T. Ichige A. Miyake N. Kanoh M. Nakata Synlett 2004 1686
- (2004) Synlett , pp. 1686
- Ichige, T.¹ Miyake, A.² Kanoh, N.³ Nakata, M.⁴

28
- 84891757019
- For a Pd-catalyzed coupling of acetyltrimethylsilane, see
- S. E. Denmark L. R. Cullen Org. Lett. 2014 16 70
- (2014) Org. Lett. , vol.16 , pp. 70
- Denmark, S.E.¹ Cullen, L.R.²

29
- 84893857849
- For a review of organocatalytic asymmetric conjugate addition, see
- S. Ramgren N. K. Garg Org. Lett. 2014 16 824
- (2014) Org. Lett. , vol.16 , pp. 824
- Ramgren, S.¹ Garg, N.K.²

30
- 70350506798
- D. Enders C. Wang J. X. Liebich Chem.-Eur. J. 2009 15 11058
- (2009) Chem.-Eur. J. , vol.15 , pp. 11058
- Enders, D.¹ Wang, C.² Liebich, J.X.³

31
- 34547463692
- S. Sulzer-Mosse A. Alexakis Chem. Commun. 2007 3123
- (2007) Chem. Commun. , pp. 3123
- Sulzer-Mosse, S.¹ Alexakis, A.²

32
- 78649855595
- Recent contributions
- D. Roca-Lopez D. Sadaba I. Delso R. P. Herrera T. Tejero P. Merino Tetrahedron: Asymmetry 2010 21 2561
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 2561
- Roca-Lopez, D.¹ Sadaba, D.² Delso, I.³ Herrera, R.P.⁴ Tejero, T.⁵ Merino, P.⁶

33
- 84857344995
- and
- D. Uraguchi Y. Ueki T. J. Ooi Chem. Sci. 2012 3 842
- (2012) Chem. Sci. , vol.3 , pp. 842
- Uraguchi, D.¹ Ueki, Y.² Ooi, T.J.³

34
- 84863611726
- G. K. S. Prakash F. Wang Z. Zhang C. Ni R. Haiges G. A. Olah Org. Lett. 2012 14 3260
- (2012) Org. Lett. , vol.14 , pp. 3260
- Prakash, G.K.S.¹ Wang, F.² Zhang, Z.³ Ni, C.⁴ Haiges, R.⁵ Olah, G.A.⁶

35
- 84862777637
- L.-Q. Lu X.-L. An J.-R. Chen W.-J. Xiao Synlett 2012 490
- (2012) Synlett , pp. 490
- Lu, L.-Q.¹ An, X.-L.² Chen, J.-R.³ Xiao, W.-J.⁴

36
- 84885102458
- O. V. Serdyuk C. M. Heckel S. B. Tsogoeva Org. Biomol. Chem. 2013 11 7051
- (2013) Org. Biomol. Chem. , vol.11 , pp. 7051
- Serdyuk, O.V.¹ Heckel, C.M.² Tsogoeva, S.B.³

37
- 84883395040
- As expected, the reaction performed in the presence of the "quasi" enantiomeric catalyst derived from quinine afforded the addition product with the opposite absolute configuration, in comparable yield (67%) and marginally lower enantioselectivity (83% ee)
- Y. Xi X. Shi Chem. Commun. 2013 8583
- (2013) Chem. Commun. , pp. 8583
- Xi, Y.¹ Shi, X.²

38
- 47149096183
- D. A. Alonso S. Kitagaki N. Utsumi C. F. Barbas Angew. Chem., Int. Ed. 2008 47 4588
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 4588
- Alonso, D.A.¹ Kitagaki, S.² Utsumi, N.³ Barbas, C.F.⁴

39
- 79955378501
- S. Rossi M. Benaglia F. Cozzi A. Genoni T. Benincori Adv. Synth. Catal. 2011 353 848
- (2011) Adv. Synth. Catal. , vol.353 , pp. 848
- Rossi, S.¹ Benaglia, M.² Cozzi, F.³ Genoni, A.⁴ Benincori, T.⁵

40
- 84865064701
- M. Bonsignore M. Benaglia F. Cozzi A. Genoni S. Rossi L. Raimondi Tetrahedron 2012 68 8251
- (2012) Tetrahedron , vol.68 , pp. 8251
- Bonsignore, M.¹ Benaglia, M.² Cozzi, F.³ Genoni, A.⁴ Rossi, S.⁵ Raimondi, L.⁶

41
- 0142072631
- Review
- T. Okino Y. Hoashi Y. Takemoto J. Am. Chem. Soc. 2003 135 12672
- (2003) J. Am. Chem. Soc. , vol.135 , pp. 12672
- Okino, T.¹ Hoashi, Y.² Takemoto, Y.³

42
- 29844448114
- Review
- Y. Takemoto Org. Biomol. Chem. 2005 3 4299
- (2005) Org. Biomol. Chem. , vol.3 , pp. 4299
- Takemoto, Y.¹

43
- 84929325947
- For a theoretical work on nitroalkenes reactivity, see
- J. Aleman A. Parra H. Jiang K. A. Jørgensen Chem.-Eur. J. 2011 17 689
- (2011) Chem.-Eur. J. , vol.17 , pp. 689
- Aleman, J.¹ Parra, A.² Jiang, H.³ Jørgensen, K.A.⁴

44
- 33750383626
- V. Rai I. N. N. Namboothiri Eur. J. Org. Chem. 2006 4693
- (2006) Eur. J. Org. Chem. , pp. 4693
- Rai, V.¹ Namboothiri, I.N.N.²

45
- 11844302258
- By employing (R,R)-diaminocyclohexane-derived catalyst B addition products of the (R)-configuration are obtained
- T. Okino Y. Hoashi T. Furukawa X. Xu Y. Takemoto J. Am. Chem. Soc. 2005 127 119
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 119
- Okino, T.¹ Hoashi, Y.² Furukawa, T.³ Xu, X.⁴ Takemoto, Y.⁵

46
- 37249064645
- references cited therein
- H. Gotoh H. Ishikawa Y. Hayashi Org. Lett. 2007 9 5307
- (2007) Org. Lett. , vol.9 , pp. 5307
- Gotoh, H.¹ Ishikawa, H.² Hayashi, Y.³

47
- 0000237762
- This approach accesses enantiomerically enriched β-substituted β-nitro esters starting from readily available β-nitroalkenes. The exact mechanism of the metal-promoted decarboxylation reaction is currently under study
- E. J. Corey B. W. Erickson J. Org. Chem. 1971 36 3553
- (1971) J. Org. Chem. , vol.36 , pp. 3553
- Corey, E.J.¹ Erickson, B.W.²

48
- 36348935182
- See the ESI for HPLC traces
- H. Liu J. Xu D. M. Du Org. Lett. 2007 9 4725
- (2007) Org. Lett. , vol.9 , pp. 4725
- Liu, H.¹ Xu, J.² Du, D.M.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.