Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids

Wei Yang; Xianyu Sun; Wenbo Yu; Rachita Rai; Jeffrey R. Deschamps; Lauren A. Mitchell; Chao Jiang; Alexander D. Mackerell; Fengtian Xue

doi:10.1021/acs.orglett.5b01350

Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids

Wei Yang, Xianyu Sun, Wenbo Yu, Rachita Rai, Jeffrey R. Deschamps, Lauren A. Mitchell, Chao Jiang, Alexander D. Mackerell, Fengtian Xue

Chemistry (Twin Cities)

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

16 Scopus citations

Abstract

A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.

Original language	English (US)
Pages (from-to)	3070-3073
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.5b01350
State	Published - Jun 19 2015

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title = "Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids",

abstract = "A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.",

author = "Wei Yang and Xianyu Sun and Wenbo Yu and Rachita Rai and Deschamps, {Jeffrey R.} and Mitchell, {Lauren A.} and Chao Jiang and Mackerell, {Alexander D.} and Fengtian Xue",

year = "2015",

month = jun,

day = "19",

doi = "10.1021/acs.orglett.5b01350",

language = "English (US)",

volume = "17",

pages = "3070--3073",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids

AU - Yang, Wei

AU - Sun, Xianyu

AU - Yu, Wenbo

AU - Rai, Rachita

AU - Deschamps, Jeffrey R.

AU - Mitchell, Lauren A.

AU - Jiang, Chao

AU - Mackerell, Alexander D.

AU - Xue, Fengtian

PY - 2015/6/19

Y1 - 2015/6/19

N2 - A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.

AB - A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.

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U2 - 10.1021/acs.orglett.5b01350

DO - 10.1021/acs.orglett.5b01350

M3 - Article

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AN - SCOPUS:84934976200

VL - 17

SP - 3070

EP - 3073

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 12

ER -

Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids

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