Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones

Ruth Gordillo; K. N. Houk

doi:10.1021/ja0525859

Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones

Ruth Gordillo, K. N. Houk

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

130 Scopus citations

Abstract

B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with α,β-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized.

Original language	English (US)
Pages (from-to)	3543-3553
Number of pages	11
Journal	Journal of the American Chemical Society
Volume	128
Issue number	11
DOIs	https://doi.org/10.1021/ja0525859
State	Published - Mar 22 2006

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja0525859

Cite this

@article{89dd7bddaf914dbf827f26129bcab18f,

title = "Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones",

abstract = "B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with α,β-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized.",

author = "Ruth Gordillo and Houk, {K. N.}",

year = "2006",

month = mar,

day = "22",

doi = "10.1021/ja0525859",

language = "English (US)",

volume = "128",

pages = "3543--3553",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones

AU - Gordillo, Ruth

AU - Houk, K. N.

PY - 2006/3/22

Y1 - 2006/3/22

N2 - B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with α,β-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized.

AB - B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with α,β-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized.

UR - http://www.scopus.com/inward/record.url?scp=33645420228&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33645420228&partnerID=8YFLogxK

U2 - 10.1021/ja0525859

DO - 10.1021/ja0525859

M3 - Article

C2 - 16536527

AN - SCOPUS:33645420228

SN - 0002-7863

VL - 128

SP - 3543

EP - 3553

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 11

ER -

Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this