Tandem Base-Promoted Ring Opening/ Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes

Kei Takeda; Eiji Kawanishi; Michiko Sasaki; Yuji Takahashi; Kentaro Yamaguchi

doi:10.1021/ol025738v

Tandem Base-Promoted Ring Opening/ Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes

Kei Takeda, Eiji Kawanishi, Michiko Sasaki, Yuji Takahashi, Kentaro Yamaguchi

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

25 Citations (Scopus)

Abstract

(matrix presented) Metalated O-silyl cyanohydrins of β-silyl-α,β-epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving a base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting allylic anion.

Original language	English
Pages (from-to)	1511-1514
Number of pages	4
Journal	Organic letters
Volume	4
Issue number	9
DOIs	https://doi.org/10.1021/ol025738v
Publication status	Published - May 2 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol025738v

Cite this

@article{ae48ccc2e5aa4dddbc32abebf8fb8738,

title = "Tandem Base-Promoted Ring Opening/ Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes",

abstract = "(matrix presented) Metalated O-silyl cyanohydrins of β-silyl-α,β-epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving a base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting allylic anion.",

author = "Kei Takeda and Eiji Kawanishi and Michiko Sasaki and Yuji Takahashi and Kentaro Yamaguchi",

year = "2002",

month = may,

day = "2",

doi = "10.1021/ol025738v",

language = "English",

volume = "4",

pages = "1511--1514",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Tandem Base-Promoted Ring Opening/ Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes

AU - Takeda, Kei

AU - Kawanishi, Eiji

AU - Sasaki, Michiko

AU - Takahashi, Yuji

AU - Yamaguchi, Kentaro

PY - 2002/5/2

Y1 - 2002/5/2

N2 - (matrix presented) Metalated O-silyl cyanohydrins of β-silyl-α,β-epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving a base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting allylic anion.

AB - (matrix presented) Metalated O-silyl cyanohydrins of β-silyl-α,β-epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving a base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting allylic anion.

UR - http://www.scopus.com/inward/record.url?scp=0042375926&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042375926&partnerID=8YFLogxK

U2 - 10.1021/ol025738v

DO - 10.1021/ol025738v

M3 - Article

C2 - 11975616

AN - SCOPUS:0042375926

SN - 1523-7060

VL - 4

SP - 1511

EP - 1514

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Tandem Base-Promoted Ring Opening/ Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this