Efficient Asymmetric Synthesis of Anti-Aldols from Bornanesultam Derived Boryl Enolates

Von Oppolzer, Wolfgang; Lienard, Philippe

doi:10.1016/S0040-4039(00)79339-7

Scientific article

Letter

English

Efficient Asymmetric Synthesis of Anti-Aldols from Bornanesultam Derived Boryl Enolates

ContributorsVon Oppolzer, Wolfgang; Lienard, Philippe

Published inTetrahedron Letters, vol. 34, no. 27, p. 4321-4324

Publication date1993

Abstract

O-Borylation of N-propionylsultam 1 provides in situ boryl enolate 6 which, at −78°C in the presence of TiCl4, reacts with aliphatic, aromatic and α,β-unsaturated aldehydes giving mostly crystalline, diastereomerically pure anti-aldols 3.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, LIENARD, Philippe. Efficient Asymmetric Synthesis of Anti-Aldols from Bornanesultam Derived Boryl Enolates. In: Tetrahedron Letters, 1993, vol. 34, n° 27, p. 4321–4324. doi: 10.1016/S0040-4039(00)79339-7

Article (Published version)

Identifiers

PID : unige:152037
DOI : 10.1016/S0040-4039(00)79339-7

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900793397

Journal ISSN0040-4039

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Efficient Asymmetric Synthesis of Anti-Aldols from Bornanesultam Derived Boryl Enolates

O-Borylation of N-propionylsultam 1 provides in situ boryl enolate 6 which, at −78°C in the presence of TiCl4, reacts with aliphatic, aromatic and α,β-unsaturated aldehydes giving mostly crystalline, diastereomerically pure anti-aldols 3.

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