Synthesis of (2S,3R)- and (2S,3S)-[3-~2H_1]-proline via highly stereoselective hydrolysis of a silyl enol ether

Paul Barraclough; Caroline A.Spray; Douglas W.Young

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Synthesis of (2S,3R)- and (2S,3S)-[3-~2H_1]-proline via highly stereoselective hydrolysis of a silyl enol ether

机译：甲硅烷基烯醇醚的高度立体选择性水解合成（2S，3R）-和（2S，3S）-[3-〜2H_1]-脯氨酸

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摘要

A straightforward synthesis of (2S)-[3,3- H_2]-proline 1c and (2S,3R)- and (2S,3S)-[3-~2H_1]-proline,1b and la,respectively,has been devised.The key step of the route to the latter compounds involves highly stereoselective hydrolysis of the silyl enol ethers 3 and 3a,respectively,with protonation (deuteriation) from the re-face of the silyl enol ether.

机译：分别设计了（2S）-[3,3-H_2]-脯氨酸1c和（2S，3R）-和（2S，3S）-[3-〜2H_1]-脯氨酸1b和la的简单合成方法制备后一种化合物的关键步骤分别涉及甲硅烷基烯醇醚3和3a的高度立体选择性水解，并从甲硅烷基烯醇醚的背面进行质子化（氘化）。

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《Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry》 |2005年第27期|共3页
作者
Paul Barraclough; Caroline A.Spray; Douglas W.Young;
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正文语种 eng
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Proline; Stereospecific deuteriation; Silyl enol ether; Metabolism;

机译：脯氨酸;立体特异性氘;甲硅烷基烯醇醚;代谢;

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1. Synthesis of (2S,3R)- and (2S,3S)-[3-~2H_1]-proline via highly stereoselective hydrolysis of a silyl enol ether [J] . Paul Barraclough, Caroline A.Spray, Douglas W.Young Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2005,第27期

机译：甲硅烷基烯醇醚的高度立体选择性水解合成（2S，3R）-和（2S，3S）-[3-〜2H_1]-脯氨酸
2. Assymetric synthesis of(2S,3R)- and(2S,3S)-[2-~(13)C;3-~2H] glutamic acid [J] . Kosuke Okuma, Akira M.Ono, Seiji Tsuchiya Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2009,第13期

机译：（2S，3R）-和（2S，3S）-[2-〜（13）C; 3-〜2H]谷氨酸的不对称合成
3. Asymmetric conjugate reductions with samarium diiodide: asymmetric synthesis of (2S,3R)- and (2S,3S)[2-H-2,3-H-2]-leucine-(S)-phenylalanine dipeptides and (2S,3R)[2-H-2,3-H-2]-phenylalanine methyl ester [J] . Davies SG, Rodriguez-Sola H, Tamayo JA, Organic & biomolecular chemistry . 2005,第8期

机译：二碘化sa的不对称共轭还原：（2S，3R）-和（2S，3S）[2-H-2,3-H-2]-亮氨酸-（S）-苯丙氨酸二肽和（2S，3R）的不对称合成[2-H-2,3-H-2]-苯丙氨酸甲酯
4. Cationic Rhodium Complex-Catalyzed Hydrosilylation of a,P-Unsaturated Carbonyl Compounds: Stereoselective Synthesis of Acyclic Silyl Enol Ethers [C] . Gen Onodera, Ryosuke Hachisuka, Satoko Kezuka Symposium on Organometallic Chemistry . 2006

机译：阳离子铑络合物催化A，P-不饱和羰基化合物：无环甲硅烷基烯醇醚的立体选择合成
5. The asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB. [D] . DeMong, Duane Eugene. 2003

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6. Enantioselective Synthesis of (2R 3S)- and (2S 3R)-444-trifluoro-N-Fmoc-O-tert-butyl-threonine and their Racemization-free Incorporation into Oligopeptides via Solid-phase Synthesis [O] . Nu Xiao, Zhong-Xing Jiang, Y. Bruce Yu -1

机译：（2R3S）-和（2S3R）-444-三氟-N-Fmoc-O-叔丁基苏氨酸的对映选择性合成及其通过固相合成将其无消旋地引入寡肽
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机译：（2R，3S）-（（（1R，2S，5R）-2-异丙基-5-甲基环己基）2-（4-溴苯基）-3-（叔丁氧基羰基氨基）-四氢呋喃-3-羧酸酯的合成和（ 2S，3R）-（（（1R，2S，5R）-2-异丙基-5-甲基环己基）2-（4-溴苯基）-3-（叔丁氧基羰基氨基）-四氢呋喃-3-羧酸酯

Synthesis of (2S,3R)- and (2S,3S)-[3-~2H_1]-proline via highly stereoselective hydrolysis of a silyl enol ether

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