Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin)

Christopher Hulme; Liang Ma; N. Vasant Kumar; Paul H. Krolikowski; Andrew C. Allen; Richard Labaudiniere

doi:10.1016/S0040-4039(99)02326-6

Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin)

Christopher Hulme, Liang Ma, N. Vasant Kumar, Paul H. Krolikowski, Andrew C. Allen, Richard Labaudiniere

Research output: Contribution to journal › Article › peer-review

64 Scopus citations

Abstract

This communication reveals a novel application of resin bound α-amino acids coupled with the UDC (Ugi/DeBOC/cyclize) strategy. Reaction with either N-BOC-α-amino aldehydes or N-BOC anthranilic acids and subsequent acid treatment allows the preparation of highly pure and diverse arrays (approx. 10000 in size) of 1,4-benzodiazepines (Wang resin) and ketopiperazines (hydroxymethyl resin), respectively. Notable for the benzodiazepine series of compounds are the five potential points of diversity available from this two-step protocol.

Original language	English (US)
Pages (from-to)	1509-1514
Number of pages	6
Journal	Tetrahedron Letters
Volume	41
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(99)02326-6
State	Published - Mar 4 2000

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)02326-6

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Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin). / Hulme, Christopher; Ma, Liang; Kumar, N. Vasant; Krolikowski, Paul H.; Allen, Andrew C.; Labaudiniere, Richard.

In: Tetrahedron Letters, Vol. 41, No. 10, 04.03.2000, p. 1509-1514.

Research output: Contribution to journal › Article › peer-review

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AU - Allen, Andrew C.

AU - Labaudiniere, Richard

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Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin)

Abstract

ASJC Scopus subject areas

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