Desymmetrization of Prochiral Diaryl Sulfoxides by an Asymmetric Sulfoxide-Magnesium Exchange

The first desymmetrizations of prochiral diaryl sulfoxides 1 by an asymmetric sulfoxide–magnesium exchange reaction are reported. The respective substrate (1), iPr2Mg, and the dilithium salt of (S)‐BINOL (which was prepared in situ) provided (S)‐configured aryl isopropyl sulfoxides 2 in up to 91 % y...

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Veröffentlicht in:	Chemistry : a European journal 2012-03, Vol.18 (11), p.3136-3140
Hauptverfasser:	Hampel, Thomas, Ruppenthal, Simon, Sälinger, Daniel, Brückner, Reinhard
Format:	Artikel
Sprache:	eng
Schlagworte:	Aromatic compounds asymmetric synthesis Asymmetry Catalysis Chemistry desymmetrization Exchange Magnesium - chemistry Molecular Structure Naphthols - chemistry organomagnesium compounds Stereoisomerism Substrates sulfoxide-magnesium exchange sulfoxides Sulfoxides - chemistry
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Zusammenfassung:	The first desymmetrizations of prochiral diaryl sulfoxides 1 by an asymmetric sulfoxide–magnesium exchange reaction are reported. The respective substrate (1), iPr2Mg, 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.
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.201103928