Molecular recognition of ketomalonates by asymmetric aldol reaction of aldehydes with secondary-amine organocatalysts

作者: Taichi Kano , Sunhwa Song , Keiji Maruoka

DOI: 10.1039/C2CC32772D

关键词:

摘要: A diastereo- and enantioselective aldol reaction between aldehydes a synthetically useful ketomalonate 1c as hydrated form was developed, either anti- or syn-aldol adducts having chiral tetrasubstituted carbon center were obtained in high enantioselectivities by use of tetrazole analogue L-proline (S)-2 an axially amino sulfonamide (S)-3 catalyst.

参考文章(61)
Xi Zhu, Aijun Lin, Ling Fang, Wei Li, Chengjian Zhu, Yixiang Cheng, In situ formed bifunctional primary amine-imine catalyst for asymmetric aldol reactions of α-keto esters. Chemistry: A European Journal. ,vol. 17, pp. 8281- 8284 ,(2011) , 10.1002/CHEM.201100200
Shinichi Ogawa, Norio Shibata, Junji Inagaki, Shuichi Nakamura, Takeshi Toru, Motoo Shiro, Cinchona-alkaloid-catalyzed enantioselective direct aldol-type reaction of oxindoles with ethyl trifluoropyruvate. Angewandte Chemie. ,vol. 46, pp. 8666- 8669 ,(2007) , 10.1002/ANIE.200703317
Ulrich Eder, Gerhard Sauer, Rudolf Wiechert, New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures Angewandte Chemie. ,vol. 10, pp. 496- 497 ,(1971) , 10.1002/ANIE.197104961
David A. Evans, Christopher S. Burgey, Marisa C. Kozlowski, Steven W. Tregay, C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Scope and Mechanism of the Catalytic Enantioselective Aldol Additions of Enolsilanes to Pyruvate Esters Journal of the American Chemical Society. ,vol. 121, pp. 686- 699 ,(1999) , 10.1021/JA982983U
Yoichi M. A. Yamada, Naoki Yoshikawa, Hiroaki Sasai, Masakatsu Shibasaki, Direct Catalytic Asymmetric Aldol Reactions of Aldehydes with Unmodified Ketones Angewandte Chemie. ,vol. 36, pp. 1871- 1873 ,(1997) , 10.1002/ANIE.199718711
Scott E. Denmark, Yu Fan, Martin D. Eastgate, Lewis base catalyzed, enantioselective aldol addition of methyl trichlorosilyl ketene acetal to ketones. Journal of Organic Chemistry. ,vol. 70, pp. 5235- 5248 ,(2005) , 10.1021/JO0506276
Anders Bøgevig, Nagaswamy Kumaragurubaran, Karl Anker Jørgensen, Direct catalytic asymmetric aldol reactions of aldehydes Chemical Communications. pp. 620- 621 ,(2002) , 10.1039/B200681B
Armando Córdova, Weibiao Zou, Pawel Dziedzic, Ismail Ibrahem, Efraim Reyes, Yongmei Xu, Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides. Chemistry: A European Journal. ,vol. 12, pp. 5383- 5397 ,(2006) , 10.1002/CHEM.200501639
Noriyuki Hara, Shuichi Nakamura, Norio Shibata, Takeshi Toru, First enantioselective synthesis of (R)-convolutamydine B and E with N-(heteroarenesulfonyl)prolinamides. Chemistry: A European Journal. ,vol. 15, pp. 6790- 6793 ,(2009) , 10.1002/CHEM.200900944