Desymmetrization of prochiral diaryl sulfoxides by an asymmetric sulfoxide-magnesium exchange

Hampel T.; Ruppenthal S.; S?linger D.; Brückner R.

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Desymmetrization of prochiral diaryl sulfoxides by an asymmetric sulfoxide-magnesium exchange

机译：通过不对称亚砜-镁交换进行手性二芳基亚砜的不对称化

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The first desymmetrizations of prochiral diaryl sulfoxides 1 by an asymmetric sulfoxide-magnesium exchange reaction are reported. The respective substrate (1), iPr _2Mg, and the dilithium salt of (S)-BINOL (which was prepared in situ) provided (S)-configured aryl isopropyl sulfoxides 2 in up to 91 % yield and with up to 91 % ee. (S)-BINOL was re-isolable in 98 % yield.

机译：报道了通过不对称亚砜-镁交换反应的前手性二芳基亚砜亚砜1的首次脱对称。相应的底物（1），iPr _2Mg和（S）-BINOL的二锂盐（原位制备）以高达91％的收率和91％ee的产率提供了（S）-构型的芳基异丙基亚砜2 。（S）-BINOL可重新分离，产率为98％。

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《Chemistry: A European journal》 |2012年第11期|共5页
作者
Hampel T.; Ruppenthal S.; S?linger D.; Brückner R.;
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asymmetric synthesis; desymmetrization; organomagnesium compounds; sulfoxide-magnesium exchange; sulfoxides;

机译：不对称合成;不对称化;有机镁化合物;亚砜-镁交换;亚砜;

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1. Desymmetrization of prochiral diaryl sulfoxides by an asymmetric sulfoxide-magnesium exchange [J] . Hampel T., Ruppenthal S., S?linger D., Chemistry: A European journal . 2012,第11期

机译：通过不对称亚砜-镁交换进行手性二芳基亚砜的不对称化
2. Two aspects of the desymmetrization of selected prochiral aromatic or vinylic dihalides: enantioselective halogen-lithium exchange and prochiral recognition in chiral liquid crystals [J] . Fan CA, Ferber B, Kagan HB, Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2008,第23期

机译：所选手性芳族或乙烯基二卤化物的脱对称化的两个方面：手性液晶中的对映选择性卤素-锂交换和手性识别
3. Difunctionalisation of arenes and heteroarenes by directed metallation and sulfoxide-magnesium exchange [J] . Melzig L., Rauhut C.B., Naredi-Rainer N., Chemistry: A European journal . 2011,第19期

机译：通过定向金属化和亚砜-镁交换将芳烃和杂芳烃双官能化
4. Asymmetric Desymmetrization of meso-Methylenecyclopropanes via Palladium-Catalyzed Silaborative C-C Cleavage [C] . Toshimichi Ohmura, Hiroki Taniguchi, Yoshiyuki Kondo Symposium on Organometallic Chemistry . 2007

机译：通过钯 - 催化的硅酰基C-C裂解甲酰基二氯丙烷的不对称脱差。
5. Isotope effects of excited-state hydrogen abstraction in ortho-methyl diaryl carbenes and the photophysics of organic molecules absorbed into gadolinium exchanged zeolites. [D] . Sonnichsen, Laura Beth. 2001

机译：邻甲基二芳基碳酸酯中激发态氢的同位素效应和and交换沸石吸收的有机分子的光物理性质。
6. Diastereocontrol in Asymmetric Allyl-Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides [O] . Laura A. Brozek, Michael J. Ardolino, James P. Morken -1

机译：Diastereocontrol不对称烯丙基烯丙基交叉偶联：用前手性烯丙基氯前手性allylboronates立体控制的反应
7. Functionalized Chiral Ionic Liquid Catalyzed Enantioselective Desymmetrizations of Prochiral Ketones via Asymmetric Michael Addition Reaction [O] . -1

机译：官能化手性离子液体通过不对称的迈克尔加成反应催化培训酮的映对促致对称的去误性反应
8. Selective Reductions. 45. Asymmetric Reduction of Prochiral Ketones by Iso-2-methyl, Iso-2-Ethyl, and (Iso-2(2-(Benzyloxy)Ethyl)Apopinocampheyl)-tert-Butylchloroboranes. Evidence for a Major Influence of the Steric Requirements of the 2-Substituent on the Efficiency of Asymmetric Reduction. [R] . Brown, H. C., Ramachandran, P. V. 1989

机译：选择性减少。 45.异-2-甲基，异-2-乙基和（异-2（2-（苄氧基）乙基）apopinocampheyl） - 叔丁基氯硼烷不对称还原前手性酮。 2-取代基的空间要求对不对称还原效率的主要影响的证据。

Desymmetrization of prochiral diaryl sulfoxides by an asymmetric sulfoxide-magnesium exchange

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