Lewis base activation of lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes

Scott E. Denmark; John R. Heemstra

doi:10.1021/ol034641l

Lewis base activation of lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes

Scott E. Denmark, John R. Heemstra

Chemistry

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

Abstract

(Matrix presented) A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield.

Original language	English (US)
Pages (from-to)	2303-2306
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	13
DOIs	https://doi.org/10.1021/ol034641l
State	Published - Jun 26 2003

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Online availability

10.1021/ol034641l

Library availability

Discover UIUC Full Text

Cite this

@article{b30ad05601ca40dda0f8c71da6f43254,

title = "Lewis base activation of lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes",

abstract = "(Matrix presented) A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield.",

author = "Denmark, {Scott E.} and Heemstra, {John R.}",

year = "2003",

month = jun,

day = "26",

doi = "10.1021/ol034641l",

language = "English (US)",

volume = "5",

pages = "2303--2306",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Lewis base activation of lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes

AU - Denmark, Scott E.

AU - Heemstra, John R.

PY - 2003/6/26

Y1 - 2003/6/26

N2 - (Matrix presented) A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield.

AB - (Matrix presented) A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield.

UR - http://www.scopus.com/inward/record.url?scp=0141853189&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0141853189&partnerID=8YFLogxK

U2 - 10.1021/ol034641l

DO - 10.1021/ol034641l

M3 - Article

C2 - 12816434

AN - SCOPUS:0141853189

SN - 1523-7060

VL - 5

SP - 2303

EP - 2306

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Lewis base activation of lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes

Abstract

ASJC Scopus subject areas

Online availability

Library availability

Related links

Fingerprint

Cite this