Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines

Ichiro Minami; Yukihiro Ohashi; Isao Shimizu; Jiro Tsuji

doi:10.1016/S0040-4039(00)94850-0

Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines

Ichiro Minami^*, Yukihiro Ohashi, Isao Shimizu, Jiro Tsuji

^*Corresponding author for this work

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

88 Citations (Scopus)

Abstract

Allylation of carbonucleophiles with allylic carbamates under neutral conditions has been studied. The C-allylation of carbonucleophile is competitive with the N-allylation of amines, and the structure of amines is crucial for the selectivity. Bulky secondary amines gave the best results. Also a new method of protection-deprotection of amines as carbamates has been developed. Smooth deprotection is possible by the palladium-catalyzed reaction of allyl carbamates with formic acid. This method is particulary useful for primary amines, including optically active amino acids.

Original language	English
Pages (from-to)	2449-2452
Number of pages	4
Journal	Tetrahedron Letters
Volume	26
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(00)94850-0
Publication status	Published - 1985

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines",

abstract = "Allylation of carbonucleophiles with allylic carbamates under neutral conditions has been studied. The C-allylation of carbonucleophile is competitive with the N-allylation of amines, and the structure of amines is crucial for the selectivity. Bulky secondary amines gave the best results. Also a new method of protection-deprotection of amines as carbamates has been developed. Smooth deprotection is possible by the palladium-catalyzed reaction of allyl carbamates with formic acid. This method is particulary useful for primary amines, including optically active amino acids.",

author = "Ichiro Minami and Yukihiro Ohashi and Isao Shimizu and Jiro Tsuji",

year = "1985",

doi = "10.1016/S0040-4039(00)94850-0",

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journal = "Tetrahedron Letters",

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T1 - Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines

AU - Minami, Ichiro

AU - Ohashi, Yukihiro

AU - Shimizu, Isao

AU - Tsuji, Jiro

PY - 1985

Y1 - 1985

N2 - Allylation of carbonucleophiles with allylic carbamates under neutral conditions has been studied. The C-allylation of carbonucleophile is competitive with the N-allylation of amines, and the structure of amines is crucial for the selectivity. Bulky secondary amines gave the best results. Also a new method of protection-deprotection of amines as carbamates has been developed. Smooth deprotection is possible by the palladium-catalyzed reaction of allyl carbamates with formic acid. This method is particulary useful for primary amines, including optically active amino acids.

AB - Allylation of carbonucleophiles with allylic carbamates under neutral conditions has been studied. The C-allylation of carbonucleophile is competitive with the N-allylation of amines, and the structure of amines is crucial for the selectivity. Bulky secondary amines gave the best results. Also a new method of protection-deprotection of amines as carbamates has been developed. Smooth deprotection is possible by the palladium-catalyzed reaction of allyl carbamates with formic acid. This method is particulary useful for primary amines, including optically active amino acids.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines

Abstract

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