A Highly Diastereomerically Enriched Benzyllithium Compound: The Molecular Structure and the Stereochemical Course of Its Transformations

• Published in: Organometallics Vol. 21; no. 15; pp. 3079 - 3081
• Main Authors: Strohmann, Carsten, Lehmen, Klaus, Wild, Kerstin, Schildbach, Daniel
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 22.07.2002; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Physical Sciences; Science & Technology; BENZYLIC LITHIUM COMPOUNDS; CHIRAL ORGANOSILICON COMPOUNDS; SUBSTITUTION-REACTIONS; BOND; CONFIGURATIONAL STABILITY
• ISSN: 0276-7333; 1520-6041
• DOI: 10.1021/om0201664

The solid state structure of the lithiated [(benzylsilyl)methyl]amine Me2Si{[R]-[CHLiPh]}(CH2SMP) [(R,S)-2] {SMP = 1-[(S)-2-(methoxymethyl)pyrrolidinyl]} and the absolute configuration at the metalated carbon center of this alkyllithium compound, which is highly diastereomerically enriched in solution, were determined by single-crystal X-ray diffraction methods. The stereochemical course of an integral sequence of transformations, starting from unmetalated [(benzylsilyl)methyl]amine 1, was experimentally clarified. For the selective reaction of [(R,S)-2] with MeI, inversion of the configuration at the metalated carbon center was found.