Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols

J. R. Falck; Anyu He; L. Manmohan Reddy; Abhijit Kundu; Deb K. Barma; A. Bandyopadhyay; Sukanta Kamila; Radha Akella; Romain Bejot; Charles Mioskowski

doi:10.1021/ol061953q

Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols

J. R. Falck, Anyu He, L. Manmohan Reddy, Abhijit Kundu, Deb K. Barma, A. Bandyopadhyay, Sukanta Kamila, Radha Akella, Romain Bejot, Charles Mioskowski

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

22 Scopus citations

Abstract

Treatment of cyclic tert-trihalomethylcarbinols with CrCl₂ in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.

Original language	English (US)
Pages (from-to)	4645-4647
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	20
DOIs	https://doi.org/10.1021/ol061953q
State	Published - Sep 28 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol061953q

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title = "Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols",

abstract = "Treatment of cyclic tert-trihalomethylcarbinols with CrCl2 in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.",

author = "Falck, {J. R.} and Anyu He and {Manmohan Reddy}, L. and Abhijit Kundu and Barma, {Deb K.} and A. Bandyopadhyay and Sukanta Kamila and Radha Akella and Romain Bejot and Charles Mioskowski",

year = "2006",

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doi = "10.1021/ol061953q",

language = "English (US)",

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journal = "Organic Letters",

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T1 - Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols

AU - Falck, J. R.

AU - He, Anyu

AU - Manmohan Reddy, L.

AU - Kundu, Abhijit

AU - Barma, Deb K.

AU - Bandyopadhyay, A.

AU - Kamila, Sukanta

AU - Akella, Radha

AU - Bejot, Romain

AU - Mioskowski, Charles

PY - 2006/9/28

Y1 - 2006/9/28

N2 - Treatment of cyclic tert-trihalomethylcarbinols with CrCl2 in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.

AB - Treatment of cyclic tert-trihalomethylcarbinols with CrCl2 in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.

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UR - http://www.scopus.com/inward/citedby.url?scp=33750035198&partnerID=8YFLogxK

U2 - 10.1021/ol061953q

DO - 10.1021/ol061953q

M3 - Article

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VL - 8

SP - 4645

EP - 4647

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols

Abstract

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