Access to functionalized steroid side chains via modified Julia olefination

Enver Cagri Izgu; Aaron C. Burns; Thomas R. Hoye

doi:10.1021/ol102936z

Access to functionalized steroid side chains via modified Julia olefination

Enver Cagri Izgu, Aaron C. Burns, Thomas R. Hoye

Chemistry (Twin Cities)

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

14 Scopus citations

Abstract

Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.

Original language	English (US)
Pages (from-to)	703-705
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	4
DOIs	https://doi.org/10.1021/ol102936z
State	Published - Feb 18 2011

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title = "Access to functionalized steroid side chains via modified Julia olefination",

abstract = "Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.",

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AU - Izgu, Enver Cagri

AU - Burns, Aaron C.

AU - Hoye, Thomas R.

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N2 - Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.

AB - Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.

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Access to functionalized steroid side chains via modified Julia olefination

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