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Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Electrophile Incorporation

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Organolithiums in Enantioselective Synthesis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 5))

Abstract

Enantioenriched sp 3-hybridized 1-oxy-alkyllithium compounds are accessible by lithiodestannylation of the appropriate chiral stannanes or by deprotonation of 1-alkyl carbamates by means of sec-butyllithium/(-)-sparteine. These are usually configurationally stable at temperatures below-40°C and are substituted by a wide array of electrophiles with strict stereoretention. When applying chiral substrates, bearing an adjacent stereogenic center, often a high internal chiral induction occurs, being the basis for an efficient kinetic resolution in the deprotonation step. α-Oxybenzyllithium derivatives are usually more easily accessible due to mesomeric stabilization, but most of these compounds undergo facile racemization or epimerization at temperatures around-70 to -78°C. The sense of stereospecificity of the electrophilic substitution is less predictable: both — retention or inversion — are common, depending on the individual situation. 1-Oxy-2-alkenyllithium reagents have similar stereochemical properties. In a number of cases configurational stability is recorded. Procedures for efficient dynamic kinetic resolution, involving a crystallization step, have been developed. In particular, 1-lithio-2-alkenyl carbamates — after titanation — are valuable homoenolate reagents for achieving highly stereoselective homoaldol reactions. Chiral 1-oxy-2-alkynyllithium derivatives allow for a facile entry to enantioenriched allenes.

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Authors and Affiliations

  1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149, Münster, Germany

    Dieter Hoppe, Felix Marr & Markus Brüggemann

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  1. Dieter Hoppe
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  2. Felix Marr
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  1. Dyson Perrins Laboratory Department of Chemistry, University of Oxford, South Parks Road, Oxford, 0X1 3QY, UK

    David M. Hodgson

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Hoppe, D., Marr, F., Brüggemann, M. (2003). Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Electrophile Incorporation. In: Hodgson, D.M. (eds) Organolithiums in Enantioselective Synthesis. Topics in Organometallic Chemistry, vol 5. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-36117-0_4

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