Abstract
The enantioselective direct cross-aldol addition between enolizable
aldehydes is of great importance because this transformation provides
access to configurationally defined β-hydroxyaldehydes.
These products in turn are valuable building blocks in total syntheses
of natural polyketide structures. This account gives an overview
of advances made in this field of organocatalysis.
1 Introduction
2 Direct Aldol Additions of Enolizable Aldehydes Catalyzed by
Proline, Proline Derivatives, and Imidazolidinone
2.1 Direct Aldol Additions Catalyzed by Proline and Proline Derivatives
2.2 Direct Aldol Additions Catalyzed by Imidazolidinone
3 Direct Aldol Additions of Enolizable Aldehydes Catalyzed by
Histidine
4 Conclusion
Key words
aldol reactions - enolizable aldehydes - asymmetric catalysis - organocatalysis - stereoselectivity
References
1
List B.
Lerner RA.
Barbas CF.
J.
Am. Chem. Soc.
2000,
122:
2395
2a
Li J.
Fu N.
Li X.
Luo S.
Cheng J.-P.
J.
Org. Chem.
2010,
75:
4501
2b
Hajra S.
Giri AK.
Hazra S.
J.
Org. Chem.
2009,
74:
7978
2c
Kano T.
Yamaguchi Y.
Maruoka K.
Chem.
Eur. J.
2009,
15:
6678
2d
Siyutkin DE.
Kucherenko AS.
Zlotin SG.
Tetrahedron
2009,
65:
1366
2e
Xiong Y.
Wang F.
Dong S.
Liu X.
Feng X.
Synlett
2008,
73
2f
Zu L.
Xie H.
Li H.
Wang J.
Wang W.
Org. Lett.
2008,
10:
1211
2g
Kano T.
Yamaguchi Y.
Tanaka Y.
Maruoka K.
Angew. Chem. Int. Ed.
2007,
46:
1738
2h
Hayashi Y.
Aratake S.
Itoh T.
Okano T.
Sumiya T.
Shoji M.
Chem.
Commun. (Cambridge)
2007,
957
with the exception of the reaction between dimethoxyacetaldehyde
and hydrocinnamaldehyde
2i
Luo S.
Li J.
Xu H.
Zhang L.
Cheng J.-P.
Org. Lett.
2007,
9:
3675
2j
Mase N.
Nakai Y.
Ohara N.
Yoda H.
Takabe K.
Tanaka F.
Barbas CF.
J.
Am. Chem. Soc.
2006,
128:
734
2k
Zhang F.
Su N.
Gong Y.
Synlett
2006,
1703
2l
Zhang S.
Duan W.
Wang W.
Adv.
Synth. Catal.
2006,
348:
1228
2m
Hayashi Y.
Urushima T.
Shoji M.
Uchimaru T.
Shiina I.
Adv.
Synth. Catal.
2005,
347:
1595
2n
Wang W.
Li H.
Wang J.
Tetrahedron
Lett.
2005,
46:
5077
3a
Northrup AB.
MacMillan DWC.
J. Am. Chem. Soc.
2002,
124:
6798
highlighted in
3b
Cauble DF.
Krische MJ.
Chemtracts
2002,
15:
380
3c
Alcaide B.
Almendros P.
Angew. Chem. Int. Ed.
2003,
42:
858
3d
Marigo M.
Melchiorre P.
ChemCatChem
2010,
2:
621
4a
Northrup AB.
Mangion IK.
Hettche F.
MacMillan DWC.
Angew. Chem. Int. Ed.
2004,
43:
2152
4b
Northrup AB.
MacMillan DWC.
Science (Washington,
DC, U.S.)
2004,
305:
1752
5
Mangion IK.
MacMillan DWC.
J. Am.
Chem. Soc.
2005,
127:
3696
6
Pihko PM.
Erkkilä A.
Tetrahedron Lett.
2003,
44:
7607
7
Smith AB.
Tomioka T.
Risatti CA.
Sperry JB.
Sfouggatakis C.
Org. Lett.
2008,
10:
4359
8
Storer RI.
MacMillan DWC.
Tetrahedron
2004,
60:
7705
9
Chowdari NS.
Ramachary DB.
Cordova A.
Barbas
CF.
Tetrahedron
Lett.
2002,
43:
9591
10
Cordova A.
Tetrahedron
Lett.
2004,
45:
3949
11
Gijsen HJM.
Wong C.-H.
J. Am. Chem.
Soc.
1995,
117:
7585
12
Casas J.
Engqvist M.
Ibrahem I.
Kaynak B.
Cordova A.
Angew.
Chem. Int. Ed.
2005,
44:
1343
13
Reyes E.
Cordova A.
Tetrahedron Lett.
2005,
46:
6605
14a
Cordova A.
Engqvist M.
Ibrahem I.
Casas J.
Sunden H.
Chem. Commun. (Cambridge)
2005,
2047
14b
Cordova A.
Ibrahem I.
Casas J.
Sunden H.
Engqvist M.
Reyes E.
Chem. Eur. J.
2005,
11:
4772
15
Zhao G.-L.
Liao W.-W.
Cordova A.
Tetrahedron
Lett.
2006,
47:
4929
16a
Kofoed J.
Reymond J.-L.
Darbre T.
Org. Biomol. Chem.
2005,
3:
1850
16b
Kofoed J.
Machuqueiro M.
Reymond J.-L.
Darbre T.
Chem. Commun. (Cambridge)
2004,
1540
17
Thayumanavan R.
Tanaka F.
Barbas CF.
Org. Lett.
2004,
6:
3541
18
Guillena G.
Najera C.
Ramon DJ.
Tetrahedron: Asymmetry
2007,
18:
2249
19 With the sole exception of cross-aldol
additions involving isobutyraldehyde as the ene component and 4-nitrobenz-aldehyde
as the carbonyl one, see: Mase N.
Tanaka F.
Barbas CF.
Angew.
Chem. Int. Ed.
2004,
43:
2420
20
Hayashi Y.
Aratake S.
Okano T.
Takahashi J.
Sumiya T.
Shoji M.
Angew. Chem. Int. Ed.
2006,
45:
5527
21
Mangion IK.
Northrup AB.
MacMillan DWC.
Angew. Chem. Int. Ed.
2004,
43:
6722
22 For chiral phosphine oxide catalysis,
see: Kotani S.
Shimoda Y.
Sugiura M.
Nakajima M.
Tetrahedron
Lett.
2009,
50:
4602
23 For primary amine catalysis, see:
ref. 2a
24
Markert M.
Mulzer M.
Schetter B.
Mahrwald R.
J. Am. Chem. Soc.
2007,
129:
7258
25a
Markert M.
Scheffler U.
Mahrwald R.
J. Am. Chem. Soc.
2009,
131:
16642
highlighted in
25b
Zanda M.
Synform
2010,
A16 ; DOI: 10.1055/s-0030-1259401
25c
Synfacts
2010,
101
26 Scheffler, U.; Mahrwald R. in preparation.