Efficient Preparation of Highly Optically Active (S)-(-)-2,3,-Allenols and (R)-(+)-2,3-Allenyl Acetates by a Clean Novozym-435-Catalyzed Enzymatic Separation of Racemic 2,3-Allenols

Daiwang Xu; Zuyi Li; Shengmaing Ma

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Efficient Preparation of Highly Optically Active (S)-(-)-2,3,-Allenols and (R)-(+)-2,3-Allenyl Acetates by a Clean Novozym-435-Catalyzed Enzymatic Separation of Racemic 2,3-Allenols

机译：通过干净的Novozym-435催化消旋外消旋2,3的酶促分离，高效制备高旋光性（S）-（-）-2,3，-烯丙醇和（R）-（+）-2,3-烯丙基乙酸酯-烯丙醇

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Novozyme-435 has been found to be an effective biocatalyst for the kinetic resolution of a series of racemic 2,3-allenols, affording highly optically active (S)-(-)-2,3-allenols and (R)-(+)-2,3-allenyl acetates in high yields and with excellent ee values. The reaction of 3-(n-butyl)-3,4-pentadien-2-ol (1a) was successfully performed on a 10 g scale to afford the corresponding (S)-(-)-2,3-allenol (1a) and (R)-(+)-2,3-allenyl acetate (2a) in synthetically useful amounts and with high ee values. The advantages of this reaction are the ready availability of the starting materials, high stereoselectivities for both (-)-2,3-allenols and (+)-2,3-allenyl acetates, the use of a relatively high substrate concentration, and a lower catalyst loading. The resulting (S)-(-)-2,3-allenol 1a can be converted into the corresponding chiral 2,5-dihydrofuran and the vinylic exporide.

机译：已发现Novozyme-435是一种有效的生物催化剂，可动力学拆分一系列外消旋的2,3-烯醇，提供高度旋光的（S）-（-）-2,3-烯醇和（R）-（+ ）-2,3-烯丙基乙酸酯，收率高，具有出色的ee值。 3-（正丁基）-3,4-戊二烯-2-醇（1a）的反应以10 g规模成功进行，得到了相应的（S）-（-）-2,3-allenol（1a））和（R）-（+）-2,3-烯丙基乙酸酯（2a）以合成有用的量且具有较高的ee值。该反应的优点是原料易于获得，（-）-2,3-烯丙醇和（+）-2,3-烯丙基乙酸酯的高立体选择性，使用相对高的底物浓度和催化剂用量降低。可以将所得的（S）-（-）-2，3-烯丙醇1a转化为相应的手性2，5-二氢呋喃和乙烯基exporide。

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来源
《Chemistry: A European journal》 |2002年第21期|共7页
作者
Daiwang Xu; Zuyi Li; Shengmaing Ma;
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正文语种 eng
中图分类化学;应用化学;
关键词
allenes; alcohols; enzymes; kinetic resolution;

机译：丙二烯;醇;酶;动力学拆分;

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1. Efficient Preparation of Highly Optically Active (S)-(-)-2,3,-Allenols and (R)-(+)-2,3-Allenyl Acetates by a Clean Novozym-435-Catalyzed Enzymatic Separation of Racemic 2,3-Allenols [J] . Daiwang Xu, Zuyi Li, Shengmaing Ma Chemistry: A European journal . 2002,第21期

机译：通过干净的Novozym-435催化消旋外消旋2,3的酶促分离，高效制备高旋光性（S）-（-）-2,3，-烯丙醇和（R）-（+）-2,3-烯丙基乙酸酯-烯丙醇
2. Novozym-435-catalyzed efficient preparation of (1S)-ethenyl and ethynyl 2,3-allenols and (1R)-ethenyl and ethynyl 2,3-allenyl acetates with high enantiomeric excess [J] . Xu DW., Li ZY., Ma SM. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2003,第23期

机译：Novozym-435催化高效制备对映体过量的（1S）-乙烯基和乙炔基2,3-烯丙醇和（1R）-乙烯基和乙炔基2,3-烯丙基乙酸酯
3. An Efficient CuCN-Catalyzed Synthesis of Optically Active 2,3-Allenols from Optically Active 1-Substituted 4-Chloro-2-butyn-1-ols [J] . Jing Li, Wangqing Kong, Chanting Fu, The Journal of Organic Chemistry . 2009,第14期

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4. Novel highly efficient non-fullerene acceptor based on naphtho[2,3-b]thiophene diimidefor organic solar cells [C] . Johan Hamonnet, Masahiro Nakano, Kyohei Nakano, 応用物理学会春季学術講演会;応用物理学会 . 2018

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7. Construction of Chiral 2,3-Allenols through Copper(I)-Catalyzed Asymmetric Direct Alkynylogous Aldol Reaction [O] . Guangyao Ran, Yingchun Chen 2020

机译：通过铜（I）构建手性2,3-甲苯烯醇 - 催化不对称直接炔基醛醇反应

Efficient Preparation of Highly Optically Active (S)-(-)-2,3,-Allenols and (R)-(+)-2,3-Allenyl Acetates by a Clean Novozym-435-Catalyzed Enzymatic Separation of Racemic 2,3-Allenols

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