A Three Component Coupling Approach to a Chiral 1β-Methylcarbapenem Key Intermediate

Naofumi Tsukada; Takashi Shimada; Young Soo Gyoung; Naoki Asao; Yoshinori Yamamoto

doi:10.1021/jo00106a027

A Three Component Coupling Approach to a Chiral 1β-Methylcarbapenem Key Intermediate

Naofumi Tsukada, Takashi Shimada, Young Soo Gyoung, Naoki Asao, Yoshinori Yamamoto

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58 Citations (Scopus)

Abstract

Conjugate addition of N-benzyl-N-(R)-1-phenylethyl)amme (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1β-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.

Original language	English
Pages (from-to)	143-148
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	60
Issue number	1
DOIs	https://doi.org/10.1021/jo00106a027
Publication status	Published - 1995 Jan 1

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Organic Chemistry

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title = "A Three Component Coupling Approach to a Chiral 1β-Methylcarbapenem Key Intermediate",

abstract = "Conjugate addition of N-benzyl-N-(R)-1-phenylethyl)amme (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1β-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.",

author = "Naofumi Tsukada and Takashi Shimada and Gyoung, {Young Soo} and Naoki Asao and Yoshinori Yamamoto",

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AU - Tsukada, Naofumi

AU - Shimada, Takashi

AU - Gyoung, Young Soo

AU - Asao, Naoki

AU - Yamamoto, Yoshinori

PY - 1995/1/1

Y1 - 1995/1/1

N2 - Conjugate addition of N-benzyl-N-(R)-1-phenylethyl)amme (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1β-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.

AB - Conjugate addition of N-benzyl-N-(R)-1-phenylethyl)amme (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1β-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.

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A Three Component Coupling Approach to a Chiral 1β-Methylcarbapenem Key Intermediate

Abstract

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