Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides

Hideo Nagashima; Hidetoshi Wakamatsu; Nobuyasu Ozaki; Tsutomu Ishii; Masakazu Watanabe; Tomonori Tajima; Kenji Itoh

doi:10.1021/jo00032a016

Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides

Hideo Nagashima, Hidetoshi Wakamatsu, Nobuyasu Ozaki, Tsutomu Ishii, Masakazu Watanabe, Tomonori Tajima, Kenji Itoh

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

108 Citations (Scopus)

Abstract

A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated γ-lactams from allylic alcohols. No δ-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

Original language	English
Pages (from-to)	1682-1689
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	57
Issue number	6
DOIs	https://doi.org/10.1021/jo00032a016
Publication status	Published - Mar 1 1992
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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Nagashima, H., Wakamatsu, H., Ozaki, N., Ishii, T., Watanabe, M., Tajima, T., & Itoh, K. (1992). Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides. Journal of Organic Chemistry, 57(6), 1682-1689. https://doi.org/10.1021/jo00032a016

Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides. / Nagashima, Hideo; Wakamatsu, Hidetoshi; Ozaki, Nobuyasu et al.
In: Journal of Organic Chemistry, Vol. 57, No. 6, 01.03.1992, p. 1682-1689.

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

Nagashima, H, Wakamatsu, H, Ozaki, N, Ishii, T, Watanabe, M, Tajima, T & Itoh, K 1992, 'Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides', Journal of Organic Chemistry, vol. 57, no. 6, pp. 1682-1689. https://doi.org/10.1021/jo00032a016

Nagashima H, Wakamatsu H, Ozaki N, Ishii T, Watanabe M, Tajima T et al. Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides. Journal of Organic Chemistry. 1992 Mar 1;57(6):1682-1689. doi: 10.1021/jo00032a016

Nagashima, Hideo ; Wakamatsu, Hidetoshi ; Ozaki, Nobuyasu et al. / Transition Metal Catalyzed Radical Cyclization : New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides. In: Journal of Organic Chemistry. 1992 ; Vol. 57, No. 6. pp. 1682-1689.

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AU - Nagashima, Hideo

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Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides

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