Asymmetric conjugate reduction of alpha,beta-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts

Kanazawa Y; Tsuchiya Y; Kobayashi K; Shiomi T; Itoh J; Kikuchi M; Yamamoto Y; Nishiyama H

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Asymmetric conjugate reduction of alpha,beta-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts

机译：手性铑（2,6-二恶唑啉基苯基）催化剂对α，β-不饱和酮和酯的不对称共轭还原

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New asymmetric conjugate reduction of beta,beta-disubstituted alpha,beta-unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6-bisoxazolinylphenyl) complexes in high yields and high en antioselectivity. (E)-4Phenyl-3-penten-2-one and (E)-4-phenyl-4-isopropyl-3-penten-2-one were readily reduced at 60 degrees C in 95% ee and 98% ee, respectively, by 1 mol% of catalyst loading. (EtO)(2)MeSiH proved to be the best hydrogen donor of choice. tert-Butyl (E)-beta-methylcinnamate and beta-isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98% ee.

机译：在手性铑（2,6-双恶唑啉基苯基）络合物存在下，用烷氧基氢硅烷以高收率和高对映选择性实现了β，β-二取代的α，β-不饱和酮和酯的新不对称共轭还原。（E）-4苯基-3-戊烯-2-酮和（E）-4-苯基-4-异丙基-3-戊烯-2-酮在60°C时容易分别在95％ee和98％ee中还原催化剂负载量的1摩尔％。（EtO）（2）MeSiH被证明是最佳的氢供体选择。（E）-β-甲基肉桂酸叔丁酯和β-异丙基肉桂酸酯也可以还原为相应的二氢肉桂酸酯衍生物，ee最高可达98％。

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《Chemistry: A European journal》 |2005年第1期|共9页
作者
Kanazawa Y; Tsuchiya Y; Kobayashi K; Shiomi T; Itoh J; Kikuchi M; Yamamoto Y; Nishiyama H;
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正文语种 eng
中图分类化学;
关键词
asymmetric catalysis; conjugate reduction; hydrosilanes; oxazolines; rhodium; BIS(OXAZOLINYL)PHENYLRHODIUM(III) AQUA COMPLEXES; SEMICORRIN COBALT CATALYSTS; ALDOL-TYPE CONDENSATION; CARBONYL-COMPOUNDS; ENANTIOSELECTIVE ALLYLATION; COPPER(I) SALT; HOMOENOLATE EQUIVALENTS; ABSOLUTE-CONFIGURATION; MICHAEL ADDITION; ACYCLIC ENONES;

机译：不对称催化;共轭还原;氢硅烷;恶唑啉;铑;BIS（恶唑啉基）苯基铑（III）水络合物;半可可钴催化剂;ALDOL型缩合;羰基化合物;对映选择性烯化;铜（I）盐;均一构型;迈克尔加成;环烯;

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1. Asymmetric Conjugate Reduction of alpha,beta-Unsaturated Ketones and Esters with Chiral Rhodium(2,6-bisoxazolinylphenyl) Catalysts [J] . Yoshinori Kanazawa, Yasunori Tsuchiya, Kazuki Kobayashi, Chemistry: A European journal . 2006,第1期

机译：手性铑（2,6-二恶唑啉基苯基）催化剂不对称共轭还原α，β-不饱和酮和酯
2. Asymmetric conjugate reduction of alpha,beta-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts [J] . Kanazawa Y, Tsuchiya Y, Kobayashi K, Chemistry: A European journal . 2005,第1期

机译：手性铑（2,6-二恶唑啉基苯基）催化剂对α，β-不饱和酮和酯的不对称共轭还原
3. Asymmetric conjugate reduction of alpha,beta-unsaturated esters with chiral rhodium(bisoxazolinylphenyl) catalysts [J] . Tsuchiya Y, Kanazawa Y, Shiomi T, Synlett . 2004,第14期

机译：手性铑（双恶唑啉基苯基）催化剂对α，β-不饱和酯的不对称共轭还原
4. 1,4-Addition of Arylboronic Acids to p-Aryl-alpha,beta-unsaturated Ketones and Esters Catalyzed by a Rhodium(I)-chiraphos Complex [C] . Takashi Nishikata, Tetsuji Iyama, Hiroto Tachikawa Symposium on Organometallic Chemistry . 2006

机译：1,4-加入芳基硼酸至p-芳基-α，β-不饱和酮和由铑（I）催化的酯 - 富铬络合物
5. The epoxidation of dienes, alpha,beta-unsaturated ketones, alpha,beta-unsaturated esters and vinyl esters by dimethyldioxirane. [D] . Chen, Hsinhung. 2001

机译：二烯，α，β-不饱和酮，α，β-不饱和酯和乙烯基酯被二甲基二环氧乙烷环氧化。
6. Efficient Synthesis of Chiral Trisubstituted 12‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes [O] . Qian Yao, Yuting Liao, Dr. Lili Lin, -1

机译：丙二酸酯向烯炔的催化不对称共轭加成反应高效合成手性三取代12-烯基酮
7. Conjugate Additions of Grignard Reagents to alpha, beta-Unsaturated Esters. XV. Reactions with Octa-2,4,6-trienoic Ester. General Discussion of the Conjugate Addition Reaction. [O] . Steffen Jacobsen, Aage Jart, Ture Kindt-Larsen, 1963

机译：将GRIGNARD试剂的共轭添加至α，β-不饱和酯。 XV。用Octa-2,4,6-三烯酯的反应。缀合物添加反应的一般讨论。

Asymmetric conjugate reduction of alpha,beta-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts

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