Chiral toluene-2,α-sultam auxiliaries: asymmetric alkylations, acylations and aldolizations of N-acyl derivatives

Von Oppolzer, Wolfgang; Rodriguez, Ines; Starkemann, Christian; Walther, Eric Pierre Ernest

doi:10.1016/S0040-4039(00)97794-3

Scientific article

Letter

English

Chiral toluene-2,α-sultam auxiliaries: asymmetric alkylations, acylations and aldolizations of N-acyl derivatives

ContributorsVon Oppolzer, Wolfgang; Rodriguez, Ines; Starkemann, Christian; Walther, Eric Pierre Ernest

Published inTetrahedron Letters, vol. 31, no. 35, p. 5019-5022

Publication date1990

Abstract

Successive treatment of (R)-N-acylsultams 4 with NHDMS/alkyl halides or NHDMS/acyl chlorides provides alkylated or acylated products 6 or 7. Diastereoselective reductions of 7 with Zn(BH₄)₂ or NaHB(sBu)₃ gives “syn”- or “anti”-aldols 8 or 9. Reaction of 4 with BEt₃/TfOH/EtN(iPr)₂ followed by addition of aromatic or aliphatic aldehydes affords diastereomerically pure “syn”-aldols 10. Non-destructive removal of auxiliary 3 from 6, 8, 9 and 10 yields enantiomerically pure products 12 to 16.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. Chiral toluene-2,α-sultam auxiliaries: asymmetric alkylations, acylations and aldolizations of N-acyl derivatives. In: Tetrahedron Letters, 1990, vol. 31, n° 35, p. 5019–5022. doi: 10.1016/S0040-4039(00)97794-3

Article (Published version)

Identifiers

PID : unige:152792
DOI : 10.1016/S0040-4039(00)97794-3

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900977943

Journal ISSN0040-4039

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Chiral toluene-2,α-sultam auxiliaries: asymmetric alkylations, acylations and aldolizations of N-acyl derivatives

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