Asymmetric Michael Addition of Malonates to Enones Catalyzed by a Primary β-Amino Acid and Its Lithium Salt
作者： Masanori Yoshida , Mao Narita , Shoji Hara
DOI: 10.1021/JO201429W
关键词: Reaction mechanism 、 Primary (chemistry) 、 Amino acid 、 Enantioselective synthesis 、 Organic chemistry 、 Chemistry 、 Michael reaction 、 Lithium 、 Salt (chemistry) 、 Catalysis
摘要: Highly enantioselective Michael addition of malonates to enones was achieved using a mixed catalyst consisting primary β-amino acid, O-TBDPS (S)-β-homoserine, and its lithium salt. Various cyclic acyclic were converted into 1,5-ketoesters in high yields (up 92%) with enantioselectivity 97% ee) under mild reaction conditions. Details synthesis the catalyst, optimization conditions for reaction, plausible mechanism are described.
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sci-hub.se 参考文章(49)
Tadao HAYAKAWAH, Hisao NISHI, Junzo NOGUCHI, Shoichi IKEDA, Takuya YAMASHITA, Toshizo ISEMURA, タンパク質類似物質合成法に関する研究(第23～25報) (第24報)α-アミノ-α,ω-ジカルボン酸-ω-ベンジルエステルの製法ならびにそれらの重合物の性質 Nippon Kagaku Kaishi. ,vol. 82, pp. 601- 604 ,(1961) , 10.1246/NIKKASHI1948.82.5_601
Masanori Yoshida, Yasunobu Ohno, Shoji Hara, Organocatalytic asymmetric thio-Michael addition of arylmethyl mercaptans to cyclic enones by a primary amino acid Tetrahedron Letters. ,vol. 51, pp. 5134- 5136 ,(2010) , 10.1016/J.TETLET.2010.07.089
Diana Almaşi, Diego A. Alonso, Carmen Nájera, Organocatalytic asymmetric conjugate additions Tetrahedron-asymmetry. ,vol. 18, pp. 299- 365 ,(2007) , 10.1016/J.TETASY.2007.01.023
Ross P. McGeary, Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride Tetrahedron Letters. ,vol. 39, pp. 3319- 3322 ,(1998) , 10.1016/S0040-4039(98)00480-8
Atsushi Sato, Masanori Yoshida, Shoji Hara, Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with β-nitroalkenes Chemical Communications. pp. 6242- 6244 ,(2008) , 10.1039/B814804J
Akihiro Kawara, Takeo Taguchi, An enantioselective Michael addition of soft nucleophiles to prochiral enone catalyzed by (2-pyrrolidyl)alkyl ammonium hydroxide Tetrahedron Letters. ,vol. 35, pp. 8805- 8808 ,(1994) , 10.1016/S0040-4039(00)78503-0
Masahiko Yamaguchi, Naoyuki Yokota, Toru Minami, The Michael addition of dimethyl malonate to α,β-unsaturated aldehydes catalysed by proline lithium salt Journal of The Chemical Society, Chemical Communications. pp. 1088- 1089 ,(1991) , 10.1039/C39910001088
Guillaume Burtin, Pierre-Jean Corringer, Douglas W. Young, Tetrahydro-1,3-oxazin-6-ones as templates for the stereoselective synthesis of β-substituted L-aspartic acids Journal of The Chemical Society-perkin Transactions 1. pp. 3451- 3459 ,(2000) , 10.1039/B004772O
Magno Agostinho, Shū Kobayashi, Strontium-Catalyzed Highly Enantioselective Michael Additions of Malonates to Enones Journal of the American Chemical Society. ,vol. 130, pp. 2430- 2431 ,(2008) , 10.1021/JA710332H
Svetlana B. Tsogoeva, Recent Advances in Asymmetric Organocatalytic 1,4-Conjugate Additions European Journal of Organic Chemistry. ,vol. 2007, pp. 1701- 1716 ,(2007) , 10.1002/EJOC.200600653