Asymmetric Organocatalyzed Direct Aldol Additions of Enolizable Aldehydes

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

aldol reactions - enolizable aldehydes - asymmetric ­catalysis - organocatalysis - stereoselectivity

References

<A NAME="RA59411ST-1">1</A> List B. Lerner RA. Barbas CF. J. Am. Chem. Soc.  2000,  122:  2395 

<A NAME="RA59411ST-2A">2a</A> Li J. Fu N. Li X. Luo S. Cheng J.-P. J. Org. Chem.  2010,  75:  4501 

<A NAME="RA59411ST-2B">2b</A> Hajra S. Giri AK. Hazra S. J. Org. Chem.  2009,  74:  7978 

<A NAME="RA59411ST-2C">2c</A> Kano T. Yamaguchi Y. Maruoka K. Chem. Eur. J.  2009,  15:  6678 

<A NAME="RA59411ST-2D">2d</A> Siyutkin DE. Kucherenko AS. Zlotin SG. Tetrahedron  2009,  65:  1366 

<A NAME="RA59411ST-2E">2e</A> Xiong Y. Wang F. Dong S. Liu X. Feng X. Synlett  2008,  73 

<A NAME="RA59411ST-2F">2f</A> Zu L. Xie H. Li H. Wang J. Wang W. Org. Lett.  2008,  10:  1211 

<A NAME="RA59411ST-2G">2g</A> Kano T. Yamaguchi Y. Tanaka Y. Maruoka K. Angew. Chem. Int. Ed.  2007,  46:  1738 

<A NAME="RA59411ST-2H">2h</A> 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

<A NAME="RA59411ST-2I">2i</A> Luo S. Li J. Xu H. Zhang L. Cheng J.-P. Org. Lett.  2007,  9:  3675 

<A NAME="RA59411ST-2J">2j</A> Mase N. Nakai Y. Ohara N. Yoda H. Takabe K. Tanaka F. Barbas CF. J. Am. Chem. Soc.  2006,  128:  734 

<A NAME="RA59411ST-2K">2k</A> Zhang F. Su N. Gong Y. Synlett  2006,  1703 

<A NAME="RA59411ST-2L">2l</A> Zhang S. Duan W. Wang W. Adv. Synth. Catal.  2006,  348:  1228 

<A NAME="RA59411ST-2M">2m</A> Hayashi Y. Urushima T. Shoji M. Uchimaru T. Shiina I. Adv. Synth. Catal.  2005,  347:  1595 

<A NAME="RA59411ST-2N">2n</A> Wang W. Li H. Wang J. Tetrahedron Lett.  2005,  46:  5077 

<A NAME="RA59411ST-3A">3a</A> Northrup AB. MacMillan DWC. J. Am. Chem. Soc.  2002,  124:  6798 

highlighted in

<A NAME="RA59411ST-3B">3b</A> Cauble DF. Krische MJ. Chemtracts  2002,  15:  380 

<A NAME="RA59411ST-3C">3c</A> Alcaide B. Almendros P. Angew. Chem. Int. Ed.  2003,  42:  858 

<A NAME="RA59411ST-3D">3d</A> Marigo M. Melchiorre P. ChemCatChem  2010,  2:  621 

<A NAME="RA59411ST-4A">4a</A> Northrup AB. Mangion IK. Hettche F. MacMillan DWC. Angew. Chem. Int. Ed.  2004,  43:  2152 

<A NAME="RA59411ST-4B">4b</A> Northrup AB. MacMillan DWC. Science (Washington, DC, U.S.)  2004,  305:  1752 

<A NAME="RA59411ST-5">5</A> Mangion IK. MacMillan DWC. J. Am. Chem. Soc.  2005,  127:  3696 

<A NAME="RA59411ST-6">6</A> Pihko PM. Erkkilä A. Tetrahedron Lett.  2003,  44:  7607 

<A NAME="RA59411ST-7">7</A> Smith AB. Tomioka T. Risatti CA. Sperry JB. Sfouggatakis C. Org. Lett.  2008,  10:  4359 

<A NAME="RA59411ST-8">8</A> Storer RI. MacMillan DWC. Tetrahedron  2004,  60:  7705 

<A NAME="RA59411ST-9">9</A> Chowdari NS. Ramachary DB. Cordova A. Barbas CF. Tetrahedron Lett.  2002,  43:  9591 

<A NAME="RA59411ST-10">10</A> Cordova A. Tetrahedron Lett.  2004,  45:  3949 

<A NAME="RA59411ST-11">11</A> Gijsen HJM. Wong C.-H. J. Am. Chem. Soc.  1995,  117:  7585 

<A NAME="RA59411ST-12">12</A> Casas J. Engqvist M. Ibrahem I. Kaynak B. Cordova A. Angew. Chem. Int. Ed.  2005,  44:  1343 

<A NAME="RA59411ST-13">13</A> Reyes E. Cordova A. Tetrahedron Lett.  2005,  46:  6605 

<A NAME="RA59411ST-14A">14a</A> Cordova A. Engqvist M. Ibrahem I. Casas J. Sunden H. Chem. Commun. (Cambridge)  2005,  2047 

<A NAME="RA59411ST-14B">14b</A> Cordova A. Ibrahem I. Casas J. Sunden H. Engqvist M. Reyes E. Chem. Eur. J.  2005,  11:  4772 

<A NAME="RA59411ST-15">15</A> Zhao G.-L. Liao W.-W. Cordova A. Tetrahedron Lett.  2006,  47:  4929 

<A NAME="RA59411ST-16A">16a</A> Kofoed J. Reymond J.-L. Darbre T. Org. Biomol. Chem.  2005,  3:  1850 

<A NAME="RA59411ST-16B">16b</A> Kofoed J. Machuqueiro M. Reymond J.-L. Darbre T. Chem. Commun. (Cambridge)  2004,  1540 

<A NAME="RA59411ST-17">17</A> Thayumanavan R. Tanaka F. Barbas CF. Org. Lett.  2004,  6:  3541 

<A NAME="RA59411ST-18">18</A> Guillena G. Najera C. Ramon DJ. Tetrahedron: Asymmetry  2007,  18:  2249 

<A NAME="RA59411ST-19">19</A> 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 

<A NAME="RA59411ST-20">20</A> Hayashi Y. Aratake S. Okano T. Takahashi J. Sumiya T. Shoji M. Angew. Chem. Int. Ed.  2006,  45:  5527 

<A NAME="RA59411ST-21">21</A> Mangion IK. Northrup AB. MacMillan DWC. Angew. Chem. Int. Ed.  2004,  43:  6722 

<A NAME="RA59411ST-22">22</A> For chiral phosphine oxide catalysis, see: Kotani S. Shimoda Y. Sugiura M. Nakajima M. Tetrahedron Lett.  2009,  50:  4602 

<A NAME="RA59411ST-23">23</A>

For primary amine catalysis, see: ref. 2a

<A NAME="RA59411ST-24">24</A> Markert M. Mulzer M. Schetter B. Mahrwald R. J. Am. Chem. Soc.  2007,  129:  7258 

<A NAME="RA59411ST-25A">25a</A> Markert M. Scheffler U. Mahrwald R. J. Am. Chem. Soc.  2009,  131:  16642 

highlighted in

<A NAME="RA59411ST-25B">25b</A> Zanda M. Synform  2010,  A16 ; DOI: 10.1055/s-0030-1259401

<A NAME="RA59411ST-25C">25c</A> Synfacts  2010,  101 

<A NAME="RA59411ST-26">26</A>

Scheffler, U.; Mahrwald R. in preparation.