Palladium-catalyzed alkylation of unactivated C(sp 3 )-H bonds with primary alkyl iodides at room temperature: Facile synthesis of β-alkyl α-amino acids

B. Wang, X. Wu, R. Jiao, S. Y. Zhang, W. A. Nack, G. He, G. Chen

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

An efficient protocol for the synthesis of β-alkyl α-amino acids via palladium-catalyzed β-C(sp 3 )-H alkylation of aminoquinoline-coupled phthaloyl alanine is developed. The new TFA-promoted reaction conditions provide excellent C-H alkylation reactivity with alkyl iodides bearing moderately electronwithdrawing groups at room temperature. A range of β-alkyl α-amino acid products, including some difficult to access by other means, can be quickly prepared from readily available primary alkyl iodides and alanine precursors.

Original languageEnglish (US)
Pages (from-to)1318-1321
Number of pages4
JournalOrganic Chemistry Frontiers
Volume2
Issue number10
DOIs
StatePublished - Oct 1 2015

Fingerprint

Alkylation
Palladium
Iodides
Alanine
Bearings (structural)
Aminoquinolines
Amino Acids
Temperature

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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abstract = "An efficient protocol for the synthesis of β-alkyl α-amino acids via palladium-catalyzed β-C(sp 3 )-H alkylation of aminoquinoline-coupled phthaloyl alanine is developed. The new TFA-promoted reaction conditions provide excellent C-H alkylation reactivity with alkyl iodides bearing moderately electronwithdrawing groups at room temperature. A range of β-alkyl α-amino acid products, including some difficult to access by other means, can be quickly prepared from readily available primary alkyl iodides and alanine precursors.",
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Palladium-catalyzed alkylation of unactivated C(sp 3 )-H bonds with primary alkyl iodides at room temperature : Facile synthesis of β-alkyl α-amino acids. / Wang, B.; Wu, X.; Jiao, R.; Zhang, S. Y.; A. Nack, W.; He, G.; Chen, G.

In: Organic Chemistry Frontiers, Vol. 2, No. 10, 01.10.2015, p. 1318-1321.

Research output: Contribution to journalArticle

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T1 - Palladium-catalyzed alkylation of unactivated C(sp 3 )-H bonds with primary alkyl iodides at room temperature

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AU - Wu, X.

AU - Jiao, R.

AU - Zhang, S. Y.

AU - A. Nack, W.

AU - He, G.

AU - Chen, G.

PY - 2015/10/1

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