Abstract
The isoborneol-10-sulfonamide unit represents a new type of chiral structure that has been successfully prepared and used in different reactions of organometallic addition to aldehydes and ketones. The obtained results were excellent in some cases, and this type of ligand is unique as it is able to promote the enantioselective addition of dialkylzinc reagents to simple ketones. The scope of these catalyzed reactions, together with some synthetic applications, is outlined. References to important related work from others are also included.
1 Introduction
2 First-Generation Ligands
2.1 Enantioselective Addition of Organozinc Reagents to Aldehydes
2.2 Enantioselective Addition to Ketones
3 Second-Generation Ligands
3.1 Enantioselective Addition of Organozinc Reagents to Aldehydes
3.2 Enantioselective Addition to Ketones
4 Third-Generation Ligands
5 Outlook
Key words
addition reactions - aldehydes - asymmetric catalysis - ketones - ligands
References
1a Chirality in Industry
Collins AN.
Sheldrake GN.
Crosby J.
John Wiley & Sons;
Chichester:
1992.
1b Process Chemistry in the Pharmaceutical Industry
Gadamasetti KG.
Marcel Dekker;
New York:
1999.
1c Blaser HU.
Spindler F.
Studer M.
Appl. Catal., A
2001,
221:
119
1d Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions
Blaser HU.
Schmidt E.
Wiley-VCH;
Weinheim:
2004.
1e Wu G.
Huang M.
Chem. Rev.
2006,
106:
2596
2 Farina V.
Reeves JT.
Senanayake CH.
Song JJ.
Chem. Rev.
2006,
106:
2734
3 Stereoselective Synthesis , In Houben-Weyl
Vol. E21:
Helmchen G.
Hoffmann RW.
Mulzer J.
Schaumann E.
Thieme;
Stuttgart:
1996.
4a Comprehensive Asymmetric Catalysis
Vols. 1-3:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
4b Comprehensive Asymmetric Catalysis
1st Suppl.:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
2004.
4c Comprehensive Asymmetric Catalysis
2nd Suppl.:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
2004.
5a Trost BM.
Science
1991,
254:
1471
5b Sheldon RA.
Pure Appl. Chem.
2000,
72:
1233
5c Trost BM.
Acc. Chem. Res.
2002,
35:
695
5d Guillena G.
Ramón DJ.
Yus M.
Angew. Chem. Int. Ed.
2007,
46:
2358
6a Yus M.
Chem. Soc. Rev.
1996,
25:
155
6b Ramón DJ.
Yus M.
Eur. J. Org. Chem.
2000,
225
6c Yus M.
Synlett
2001,
1197
6d Ramón DJ.
Yus M.
Latv. J. Chem.
2002,
79
6e Yus M. In The Chemistry of Organolithium Compounds
Rappoport Z.
Marek I.
Wiley;
Chichester:
2004.
Chap. 11.
p.647-747
7a Yus M.
Ramón DJ.
Recent Res. Dev. Org. Chem.
2002,
6:
297
7b Hatano M.
Miyamoto T.
Ishihara K.
Curr. Org. Chem.
2007,
11:
127
8a Noyori R.
Kitamura M.
Angew. Chem., Int. Ed. Engl.
1991,
30:
49
8b Soai K.
Niwa S.
Chem. Rev.
1992,
92:
833
8c Pu L.
Yu H.-B.
Chem. Rev.
2001,
101:
757
8d Pu L.
Tetrahedron
2003,
59:
9873
8e Lake F.
Moberg C.
Russ. J. Org. Chem. (Engl. Transl.)
2003,
39:
436
8f Cozzi PG.
Eur. J. Org. Chem.
2004,
4095
8g Charette AB.
Boezio AA.
Côté A.
Moreau E.
Pytkowicz J.
Desrosiers J.-N.
Legault C.
Pure Appl. Chem.
2005,
77:
1259
8h Yus M.
Ramón DJ.
Pure Appl. Chem.
2005,
77:
2111
9a Seebach D.
Beck AK.
Shiess M.
Widler L.
Wonnacott A.
Pure Appl. Chem.
1983,
55:
1807
9b Duthaler RO.
Hafner A.
Chem. Rev.
1992,
92:
807
9c Ramón DJ.
Yus M.
Recent Res. Dev. Org. Chem.
1998,
2:
489
9d Ramón DJ.
Yus M.
Chem. Rev.
2006,
106:
2126
10a Seebach D.
Plattner DA.
Beck AK.
Wang YM.
Hunziker D.
Petter W.
Helv. Chim. Acta
1992,
75:
2171
10b Ito YN.
Ariza X.
Beck AK.
Boháč A.
Ganter C.
Gawley RE.
Kühnle FNM.
Tuleja J.
Wang YM.
Seebach D.
Helv. Chim. Acta
1994,
77:
2071
10c Weber B.
Seebach D.
Tetrahedron
1994,
50:
7473
11a Balsells J.
Davis TJ.
Carroll P.
Walsh PJ.
J. Am. Chem. Soc.
2002,
124:
10336
11b Wu K.-H.
Gau H.-M.
Organometallics
2004,
23:
580
11c Pescitelli G.
Di Bari L.
Salvadori P.
Organometallics
2004,
23:
4223
12a Zalucky TB.
Malspeis L.
Patel H.
Hite G.
J. Pharm. Sci.
1965,
54:
687
12b Wolinsky J.
Dimmel DR.
Gibson TW.
J. Org. Chem.
1967,
32:
2087
12c Oppolzer W.
Chapuis C.
Kelly MJ.
Helv. Chim. Acta
1983,
66:
2358
12d Aguirre D.
Cativiela C.
Díaz de Villegas MD.
Gálvez JA.
Tetrahedron
2006,
62:
8142
13a Corey EJ.
Bernes-Seeman D.
Lee TW.
Goodman SN.
Tetrahedron Lett.
1997,
38:
6513
13b Corey EJ.
Lee TW.
Chem. Commun.
2001,
1321
14 Ramón DJ.
Yus M.
Tetrahedron: Asymmetry
1997,
8:
2479
15 Hui A.-L.
Zhang J.-T.
Wang Z.-Y.
ARKIVOC
2006,
xiii:
41
16 Hui X.-P.
Chen C.-A.
Gau H.-M.
Chirality
2005,
17:
51
17 Gadenne B.
Hesemann P.
Moreau JEJ.
Tetrahedron Lett.
2004,
45:
8157
18 Gadenne B.
Hesemann P.
Polshettiwar V.
Moreau JEJ.
Eur. J. Inorg. Chem.
2006,
3697
19 Prieto O.
Ramón DJ.
Yus M.
Tetrahedron: Asymmetry
2000,
11:
1629
20 Ramón DJ.
Yus M.
Angew. Chem. Int. Ed.
2004,
43:
284
21a Fuji K.
Chem. Rev.
1993,
93:
2037
21b Corey EJ.
Guzmán-Pérez A.
Angew. Chem. Int. Ed.
1998,
37:
388
21c Ramón DJ.
Yus M.
Curr. Org. Chem.
2004,
8:
149
21d Ramón DJ.
Yus M. In Quaternary Stereocenters: Challenges for Organic Synthesis
Christoffers J.
Baro A.
Wiley-VCH;
Weinheim:
2005.
Chap. 7.
p.207-241
21e Christoffers J.
Baro A.
Adv. Synth. Catal.
2005,
347:
1473
21f García C.
Martín VS.
Curr. Org. Chem.
2006,
10:
1849
21g Riant O.
Hannedouche J.
Org. Biomol. Chem.
2007,
5:
873
22a Boersma J. In Comprehensive Organometallic Chemistry
Vol. 2:
Wilkinson G.
Stone GA.
Abel EW.
Pergamon;
Oxford:
1982.
p.823-862
22b Noyori R.
Suga S.
Kawai K.
Okada S.
Kitamura M.
Oguni N.
Kanedo T.
Matsuda Y.
J. Organomet. Chem.
1990,
382:
19
22c Watanabe M.
Soai K.
J. Chem. Soc., Perkin Trans. 1
1994,
3125
22d Knochel P. In Encyclopaedia of Reagents for Organic Synthesis
Vol. 3:
Paquette LA.
Wiley;
Chichester:
1995.
p.1861-1866
23 Dosa PI.
Fu GC.
J. Am. Chem. Soc.
1998,
120:
445
24 Ramón DJ.
Yus M.
Tetrahedron Lett.
1998,
39:
1239
25 Ramón DJ.
Yus M.
Tetrahedron
1998,
54:
5651
26a Lu G.
Li X.
Jia X.
Chan WL.
Chan ASC.
Angew. Chem. Int. Ed.
2003,
42:
5057
26b Lu G.
Li X.
Li Y.-M.
Kwong FY.
Chan ASC.
Adv. Synth. Catal.
2006,
348:
1926
27 Yus M.
Ramón DJ.
Prieto O.
Tetrahedron: Asymmetry
2002,
13:
1573
28 Yus M.
Ramón DJ.
Prieto O.
Tetrahedron: Asymmetry
2003,
14:
1103
29 Bauer T.
Gajewiak J.
Tetrahedron
2003,
59:
10009
30 Hui A.
Zhang J.
Fan J.
Wang Z.
Tetrahedron: Asymmetry
2006,
17:
2101
31 Yus M.
Ramón DJ.
Prieto O.
Tetrahedron: Asymmetry
2002,
13:
2291
32 Forrat VJ.
Prieto O.
Ramón DJ.
Yus M.
Chem. Eur. J.
2006,
12:
4431 ; corrigendum: Chem. Eur. J. 2006 , 12 , 6727
33a García C.
LaRochelle LK.
Walsh PJ.
J. Am. Chem. Soc.
2002,
124:
10970
33b Jeon S.-J.
Li H.
García C.
LaRochelle LK.
Walsh PJ.
J. Org. Chem.
2005,
70:
448
33c Jeon S.-J.
Li H.
Walsh PJ.
J. Am. Chem. Soc.
2005,
127:
16416
33d Betancort JM.
García C.
Walsh PJ.
Synlett
2004,
749
34a Shintou T.
Mukaiyama T.
J. Am. Chem. Soc.
2004,
126:
7359
34b Mukaiyama T.
Ikegai K.
Chem. Lett.
2004,
33:
1522
35 Forrat VJ.
Ramón DJ.
Yus M.
Tetrahedron: Asymmetry
2007,
18:
400
36 Yus M.
Ramón DJ.
Prieto O.
Eur. J. Org. Chem.
2003,
2745
37 Jeon S.-J.
Walsh PJ.
J. Am. Chem. Soc.
2003,
125:
9544
38 Prieto O.
Ramón DJ.
Yus M.
Tetrahedron: Asymmetry
2003,
14:
1955
39 García C.
Walsh PJ.
Org. Lett.
2003,
5:
3641
40 Li H.
García C.
Walsh PJ.
Proc. Natl. Acad. Sci. U.S.A.
2004,
101:
5425
41a Knochel P.
Leuser H.
Gong L.-Z.
Perrone S.
Kneissel FK. In Handbook of Functionalized Organometallics: Applications in Synthesis
Vol. 1:
Knochel P.
Wiley-VCH;
Weinheim:
2005.
p.251-346
41b Schmidt F.
Stemmler RT.
Rudolph J.
Bolm C.
Chem. Soc. Rev.
2006,
35:
395
42a Li H.
Walsh PJ.
J. Am. Chem. Soc.
2004,
126:
6538
42b Li H.
Walsh PJ.
J. Am. Chem. Soc.
2005,
127:
8355
43 Walsh PJ. inventors; US Patent 6660884. The synthesis of the HOCSAC ligand, as well as its use in enantioselective alkylation processes, was patented:
; and it has been incorporated very recently into the Aldrich catalogue (no. 673315)
44 de Parrodi CA.
Walsh PJ.
Synlett
2004,
2417
45 Liu L.
Wang R.
Kang Y.-F.
Cai Chen C.
Synlett
2006,
1245
46 Forrat VJ.
Ramón DJ.
Yus M.
Tetrahedron: Asymmetry
2005,
16:
3341
47 Forrat, V. J. unpublished results.
48 Forrat VJ.
Ramón DJ.
Yus M.
Tetrahedron: Asymmetry
2006,
17:
2054
