Herstellung von Hilfsstoffen für die asymmetrische Synthese aus Weinsäure. Addition von Butyllithium an Aldehyde in chiralem Medium
Herstellung von Hilfsstoffen für die asymmetrische Synthese aus Weinsäure. Addition von Butyllithium an Aldehyde in chiralem Medium
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在 chiralem 介质中添加丁基锂和醛
DOI：
10.1002/hlca.19770600202
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发表时间：
1977
影响因子：
1.8
通讯作者：
M. Schmidt
中科院分区：
文献类型：
--
作者：
D. Seebach;H. Kalinowski;B. Bastani;G. Crass;H. Daum;H. Doêrr;N. P. Dupreez;V. Ehrig;W. Langer;C. Nüssler;H. Oei;M. Schmidt
酒石酸不对称合成助剂的制备。手性介质中丁基锂对醛类化合物的加成。
Preparation of Auxiliaries for Asymmetric Syntheses from Tartaric Acid. Additions of Butyllithium to Aldehydes in Chiral Media.
Chiral derivatives of the complexing 1,2-diheterosubstituted ethanes A–D are prepared from tartaric acid. The key starting materials are the succinic acid derivative 1, the dioxolane 2a, and the diamide 3a. These are converted to the ethers, alkoxyamines, and alkylthio-amines listed in the first column of Table 2 which also contains the derivatives 21c, 22d, and 23d made from lactic acid, malic acid, and proline, respectively. It is shown that the highest optical yields (up to 40%) in reactions of butyllithium with aldehydes are obtained when mixtures of (−)-1,2,3,4-tetramethoxy-butane (4b), (+)-2,3-dimethoxy-N,N,N′,N′-tetramethyl-1,4-butanediamine (17a), and (−)-1,4-dimethoxy-N,N,N′,N′-tetramethyl-2,3-butanediamine (14c) with pentane are used at temperatures down to −150° and ratios of auxiliary/butyllithium of up to 10:1 (see equation (1), Tables 2–4).