以商业易得的(-)-麻黄碱、(+)-伪麻黄碱和各种手性氨醇为主要原料,经过简单的两步反应,合成了一系列基于甲磺酰基的磺酰胺-氨醇(SAA)配体,并将其用于催化苯乙炔基锌对醛的不对称加成反应.在没有Ti(OiPr)4等金属试剂的条件下,配体表现出较好的不对称诱导能力,取得了高达83%ee.
Chiral methylsulfonyl-based sulfamide-amine alcohol(SAA)ligands were synthesized from commercially available starting ma terials in two simple steps.Methylsulfonyl-based SAA ligands catalyzed the asymmetric alkynylation of various aldehydes using alkynylzinc to provide chiral propargyl alcohols with moderate to good enantioselectivity up to 83%ee.
参考文献
| [1] | Trost B M;Krische M J .[J].Journal of the American Chemical Society,1999,121:6131. |
| [2] | Fox M E;Li C;Marino J P Jr;Overman L E .[J].Journal of the American Chemical Society,1999,121:5467. |
| [3] | Corey E J;Cimprich K A .[J].Journal of the American Chemical Society,1994,116:3151. |
| [4] | Si Y G;Huang H;Jiang B .[J].Chinese Journal of Inorganic Chemistry,2004,11:1389. |
| [5] | Anand N K;Carreira E M .[J].Journal of the American Chemical Society,2001,123:9687. |
| [6] | Frantz DE.;Carreira EM.;Fassler R. .Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes[J].Journal of the American Chemical Society,2000(8):1806-1807. |
| [7] | Xu Z Q;Wang R;Xu J K;Da C S,Yan W J,Chen C .[J].Angewandte Chemie International Edition,2003,42:5747. |
| [8] | Xu Z Q;Chen C;Xu J K;Miao M B,Yan W J,Wang R .[J].Organic Letters,2004,6:1193. |
| [9] | Moore D;Pu L .[J].Organic Letters,2002,4:1855. |
| [10] | Gao G;Moore D;Xie R G;Pu L .[J].Organic Letters,2002,4:4143. |
| [11] | Xu M H;Pu L .[J].Organic Letters,2002,4:4555. |
| [12] | Li X S;Lu G;Kwok W H;Chan A S C .[J].Journal of the American Chemical Society,2002,124:12636. |
| [13] | Liu, L;Wang, R;Kang, YF;Chen, C;Xu, ZQ;Zhou, YF;Ni, M;Cai, HQ;Gong, MZ .Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes[J].The Journal of Organic Chemistry,2005(3):1084-1086. |
| [14] | Kang Y F;Liu L;Wang R;Zhou Y F,Yan W J .[J].Advanced Synthesis and Catalysis,2005,347:243. |
| [15] | Ni M;Wang R;Han Z J;Mao B,Da C,Liu L,Chen C .[J].Advanced Synthesis and Catalysis,2005,347:1659. |
| [16] | Chen C;Hong L;Xu ZQ;Liu L;Wang R .Low ligand loading, highly enantioselective addition of phenylacetylene to aromatic ketones catalyzed by Schiff-base amino alcohols[J].Organic letters,2006(11):2277-2280. |
| [17] | Ding J;Shen Z X;Luo X Q;Chen W Y,Zhang Y W .[J].Chinese Journal of Chemistry,2006,24:1285. |
| [18] | Pu L .[J].Tetrahedron,2003,59:9873. |
| [19] | Cozzi P G;Hilgraf R;Zimmermann N.[J].European Journal of Organic Chemistry,2004:4095. |
| [20] | Lu G;Li Y M;Li X S;Chan A S C .[J].Coordination Chemistry Reviews,2005,249:1736. |
| [21] | Trost B M;Weiss A H .[J].Advanced Synthesis and Catalysis,2009,351:963. |
| [22] | Gao G;Xie R G;Pu L .[J].Proceedings of the National Academy of Sciences(USA),2004,101:5417. |
| [23] | Takita R;Yakura K;Ohshima T;Shibasaki M .[J].Journal of the American Chemical Society,2005,127:13760. |
| [24] | Gao G;Wang Q;Yu X Q;Xie R G,Pu L .[J].Angewandte Chemie International Edition,2006,45:122. |
| [25] | Trost B M;Weiss A H;von Wangelin A J .[J].Journal of the American Chemical Society,2006,128:8. |
| [26] | Emmerson D P G;Hems W P;Davis B G .[J].Organic Letters,2006,8:207. |
| [27] | Xu Z Q;Lin L;Xu J K;Yan W J,Wang R .[J].Advanced Synthesis and Catalysis,2006,348:506. |
| [28] | Wolf C;Liu S L .[J].Journal of the American Chemical Society,2006,128:10996. |
| [29] | Li, YM;Tang, YQ;Hui, XP;Huang, LN;Xu, PF .Synthesis of new beta-hydroxy amide ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aliphatic and vinyl aldehydes[J].Tetrahedron,2009(18):3611-3614. |
| [30] | Zhong J C;Hou S C;Bian Q H;Yin M M,Na R S,Zheng B,Li Z Y,Liu S Z,Wang M .[J].Chemistry-A European Journal,2009,15:3069. |
| [31] | Xu Z;Wu N;Ding Z H;Wang T,Mao J C,Zhang Y W .[J].Tetrahedron Letters,2009,50:926. |
| [32] | Omote M;Eto Y;Tarui A;Sato K,Ando A .[J].Tetrahedron:Asymmetry,2009,20:602. |
| [33] | Nugent W A;RajanBabu T V;Burk M J .[J].Science,1993,259:479. |
| [34] | Hawkins J M;Watson T J N .[J].Angewandte Chemie International Edition,2004,43:3224. |
| [35] | Mao J C;Wan B S;Wang R L;Wu F,Lu S W .[J].Journal of Organic Chemistry,2004,69:9123. |
| [36] | Mao J C;Wan B S;Wu F;Lu S W .[J].Chirality,2005,17:245. |
| [37] | Mao J C;Wan B S;Wu F;Lu S W .[J].Journal of Molecular Catalysis A:Chemical,2005,237:126. |
| [38] | Li H W;Huang Y B;Jin W;Xue F,Wan B S .[J].Tetrahedron Letters,2008,49:1686. |
| [39] | Cernerud M;Adolfsson H;Moberg C .[J].Tetrahedron:Asymmetry,1997,8:2655. |
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