In situ generation and nucleophilic capture of 1,n-dial equivalents from 1,n-dioates (α,ω-diesters)

Thomas R. Hoye; Lucas C. Kopel; Troy D. Ryba

doi:10.1055/s-2006-926465

In situ generation and nucleophilic capture of 1,n-dial equivalents from 1,n-dioates (α,ω-diesters)

Thomas R. Hoye, Lucas C. Kopel, Troy D. Ryba

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

14 Scopus citations

Abstract

A procedure is described for the in situ generation of functional equivalents of glutaric, succinic, and malonic dialdehydes. DIBAL-H reduction of the corresponding 1,n-dioates followed by in situ addition of a nucleophilic trapping agent allows for one-pot, bidirectional homologation. Olefination and Grignard addition classes of reactions are specifically demonstrated.

Original language	English (US)
Pages (from-to)	1572-1574
Number of pages	3
Journal	Synthesis
Issue number	10
DOIs	https://doi.org/10.1055/s-2006-926465
State	Published - May 15 2006

Keywords

Hydrides
Nucleophilic additions
Reductions
Tandem reactions
Wittig reactions

Publisher link

10.1055/s-2006-926465

Find It

Find It at U of M Libraries

Cite this

@article{f3cdaf7dfac141f28d2e724366ed2893,

title = "In situ generation and nucleophilic capture of 1,n-dial equivalents from 1,n-dioates (α,ω-diesters)",

abstract = "A procedure is described for the in situ generation of functional equivalents of glutaric, succinic, and malonic dialdehydes. DIBAL-H reduction of the corresponding 1,n-dioates followed by in situ addition of a nucleophilic trapping agent allows for one-pot, bidirectional homologation. Olefination and Grignard addition classes of reactions are specifically demonstrated.",

keywords = "Hydrides, Nucleophilic additions, Reductions, Tandem reactions, Wittig reactions",

author = "Hoye, {Thomas R.} and Kopel, {Lucas C.} and Ryba, {Troy D.}",

year = "2006",

month = may,

day = "15",

doi = "10.1055/s-2006-926465",

language = "English (US)",

pages = "1572--1574",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

}

TY - JOUR

T1 - In situ generation and nucleophilic capture of 1,n-dial equivalents from 1,n-dioates (α,ω-diesters)

AU - Hoye, Thomas R.

AU - Kopel, Lucas C.

AU - Ryba, Troy D.

PY - 2006/5/15

Y1 - 2006/5/15

N2 - A procedure is described for the in situ generation of functional equivalents of glutaric, succinic, and malonic dialdehydes. DIBAL-H reduction of the corresponding 1,n-dioates followed by in situ addition of a nucleophilic trapping agent allows for one-pot, bidirectional homologation. Olefination and Grignard addition classes of reactions are specifically demonstrated.

AB - A procedure is described for the in situ generation of functional equivalents of glutaric, succinic, and malonic dialdehydes. DIBAL-H reduction of the corresponding 1,n-dioates followed by in situ addition of a nucleophilic trapping agent allows for one-pot, bidirectional homologation. Olefination and Grignard addition classes of reactions are specifically demonstrated.

KW - Hydrides

KW - Nucleophilic additions

KW - Reductions

KW - Tandem reactions

KW - Wittig reactions

UR - http://www.scopus.com/inward/record.url?scp=33744465052&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33744465052&partnerID=8YFLogxK

U2 - 10.1055/s-2006-926465

DO - 10.1055/s-2006-926465

M3 - Article

AN - SCOPUS:33744465052

SN - 0039-7881

SP - 1572

EP - 1574

JO - Synthesis

JF - Synthesis

IS - 10

ER -

In situ generation and nucleophilic capture of 1,n-dial equivalents from 1,n-dioates (α,ω-diesters)

Abstract

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this