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

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.",

author = "Izgu, \{Enver Cagri\} and Burns, \{Aaron C.\} and Hoye, \{Thomas R.\}",

year = "2011",

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doi = "10.1021/ol102936z",

language = "English (US)",

volume = "13",

pages = "703--705",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Access to functionalized steroid side chains via modified Julia olefination

AU - Izgu, Enver Cagri

AU - Burns, Aaron C.

AU - Hoye, Thomas R.

PY - 2011/2/18

Y1 - 2011/2/18

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.

UR - https://www.scopus.com/pages/publications/79951587737

UR - https://www.scopus.com/pages/publications/79951587737#tab=citedBy

U2 - 10.1021/ol102936z

DO - 10.1021/ol102936z

M3 - Article

C2 - 21244047

AN - SCOPUS:79951587737

SN - 1523-7060

VL - 13

SP - 703

EP - 705

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Access to functionalized steroid side chains via modified Julia olefination

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