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首页> 外文期刊>Chemistry: A European journal >Lewis acid/base catalyzed [2+2]-cycloaddition of sulfenes and aldehydes: A versatile entry to chiral sulfonyl and sulfinyl derivatives
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Lewis acid/base catalyzed [2+2]-cycloaddition of sulfenes and aldehydes: A versatile entry to chiral sulfonyl and sulfinyl derivatives

机译：路易斯酸/碱催化的亚砜和醛的[2 + 2]-环加成：手性磺酰基和亚磺酰基衍生物的多用途入口

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摘要

The first catalytic asymmetric synthesis of β-sultones is reported. This development has enabled a rapid access to a number of highly enantioenriched biologically interesting sulfonyl and sulfinyl compound classes, which makes use of the inherent ring strain of the four-membered heterocycles. The products possess either two vicinal stereocenters, such as in β-hydroxy-sulfonamides, -sulfonates, -sulfones, -sulfonic acids, -sulfinic acids, γ-sultines, and γ-sultones or a single stereocenter, such as in α-branched alkyl or allyl sulfonic acids. This work also represents the first application of sulfene intermediates in asymmetric catalysis. The reactivity of a sulfene normally acting as an electrophile could be reverted by the formation of a nucleophilic zwitterionic sulfene-amine adduct. To achieve a combination of high enantioselectivity and reactivity, cooperative catalytic action of a chiral nucleophilic tertiary amine (the cinchona alkaloid derivative diydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether ((DHQ)_2PYR)) and Bi(OTf)_3 or In(OTf)_3 was of primary importance.
机译：报道了β-磺内酯的第一催化不对称合成。这一发展使得能够快速获得许多高度对映体富集的生物学上令人感兴趣的磺酰基和亚磺酰基化合物类别，这些类别利用了四元杂环的固有环应变。该产品具有两个邻位立体中心，例如在β-羟基磺酰胺，-磺酸盐，-砜，-磺酸，-亚磺酸，γ-苏氨酸和γ-内酯中，或者具有一个立体中心，例如在α-支化中。烷基或烯丙基磺酸。这项工作也代表了亚砜中间体在不对称催化中的首次应用。通常起亲电性的亚砜的反应性可通过形成亲核的两性离子亚砜-胺加合物来恢复。为了实现高对映选择性和反应性的组合，手性亲核叔胺（金鸡纳生物碱衍生物二吡喹啉2,5-二苯基-4,6-嘧啶二基二醚（（DHQ）_2PYR））和Bi（OTf）_3的协同催化作用或In（OTf）_3最重要。

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