Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: Synthesis of 3-substituted azepanes

Scott E. Denmark; Min Xie

doi:10.1021/jo071126i

Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: Synthesis of 3-substituted azepanes

Scott E. Denmark, Min Xie

Chemistry

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

Abstract

(Chemical Equation Presented) A novel γ-selective conjugate addition of 1-silyl-substituted dienol ethers to nitroalkenes activated by Lewis acids has been developed. The resulting α,β-unsaturated acylsilanes undergo photoinduced protodesilylation to afford the corresponding enals, which can be conveniently transformed into azepanes under appropriate reductive conditions.

Original language	English (US)
Pages (from-to)	7050-7053
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	18
DOIs	https://doi.org/10.1021/jo071126i
State	Published - Aug 31 2007

ASJC Scopus subject areas

Organic Chemistry

Online availability

10.1021/jo071126i

Library availability

Discover UIUC Full Text

Cite this

@article{a6b35eeb0ea74875911b86459f0b7420,

title = "Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: Synthesis of 3-substituted azepanes",

abstract = "(Chemical Equation Presented) A novel γ-selective conjugate addition of 1-silyl-substituted dienol ethers to nitroalkenes activated by Lewis acids has been developed. The resulting α,β-unsaturated acylsilanes undergo photoinduced protodesilylation to afford the corresponding enals, which can be conveniently transformed into azepanes under appropriate reductive conditions.",

author = "Denmark, {Scott E.} and Min Xie",

year = "2007",

month = aug,

day = "31",

doi = "10.1021/jo071126i",

language = "English (US)",

volume = "72",

pages = "7050--7053",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes

T2 - Synthesis of 3-substituted azepanes

AU - Denmark, Scott E.

AU - Xie, Min

PY - 2007/8/31

Y1 - 2007/8/31

N2 - (Chemical Equation Presented) A novel γ-selective conjugate addition of 1-silyl-substituted dienol ethers to nitroalkenes activated by Lewis acids has been developed. The resulting α,β-unsaturated acylsilanes undergo photoinduced protodesilylation to afford the corresponding enals, which can be conveniently transformed into azepanes under appropriate reductive conditions.

AB - (Chemical Equation Presented) A novel γ-selective conjugate addition of 1-silyl-substituted dienol ethers to nitroalkenes activated by Lewis acids has been developed. The resulting α,β-unsaturated acylsilanes undergo photoinduced protodesilylation to afford the corresponding enals, which can be conveniently transformed into azepanes under appropriate reductive conditions.

UR - http://www.scopus.com/inward/record.url?scp=34548804350&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34548804350&partnerID=8YFLogxK

U2 - 10.1021/jo071126i

DO - 10.1021/jo071126i

M3 - Article

C2 - 17676807

AN - SCOPUS:34548804350

SN - 0022-3263

VL - 72

SP - 7050

EP - 7053

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: Synthesis of 3-substituted azepanes

Abstract

ASJC Scopus subject areas

Online availability

Library availability

Related links

Fingerprint

Cite this