Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL

Christopher D. Anderson; Travis Dudding; Ruth Gordillo; K. N. Houk

doi:10.1021/ol800875k

Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL

Christopher D. Anderson, Travis Dudding, Ruth Gordillo, K. N. Houk

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

76 Scopus citations

Abstract

(Chemical Equation Presented) The asymmetric hetero-Diels-Alder reaction of benzaldehyde with 1-dimethylamino-3-tert-butyldimethylsiloxy butadiene catalyzed by (R,R)-1-Np-TADDOL was studied using computational methods. A theoretical rationale was developed through the combined use of molecular mechanics and ONIOM(B3LYP/6-31G(d):AM1) calculations. The origins of stereoselection in this process were identified, and excellent correlation between experiment and theory was found.

Original language	English (US)
Pages (from-to)	2749-2752
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	13
DOIs	https://doi.org/10.1021/ol800875k
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol800875k

Cite this

@article{f2ff08ef51e74d889196722bd8717ec2,

title = "Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL",

abstract = "(Chemical Equation Presented) The asymmetric hetero-Diels-Alder reaction of benzaldehyde with 1-dimethylamino-3-tert-butyldimethylsiloxy butadiene catalyzed by (R,R)-1-Np-TADDOL was studied using computational methods. A theoretical rationale was developed through the combined use of molecular mechanics and ONIOM(B3LYP/6-31G(d):AM1) calculations. The origins of stereoselection in this process were identified, and excellent correlation between experiment and theory was found.",

author = "Anderson, {Christopher D.} and Travis Dudding and Ruth Gordillo and Houk, {K. N.}",

year = "2008",

doi = "10.1021/ol800875k",

language = "English (US)",

volume = "10",

pages = "2749--2752",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL

AU - Anderson, Christopher D.

AU - Dudding, Travis

AU - Gordillo, Ruth

AU - Houk, K. N.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) The asymmetric hetero-Diels-Alder reaction of benzaldehyde with 1-dimethylamino-3-tert-butyldimethylsiloxy butadiene catalyzed by (R,R)-1-Np-TADDOL was studied using computational methods. A theoretical rationale was developed through the combined use of molecular mechanics and ONIOM(B3LYP/6-31G(d):AM1) calculations. The origins of stereoselection in this process were identified, and excellent correlation between experiment and theory was found.

AB - (Chemical Equation Presented) The asymmetric hetero-Diels-Alder reaction of benzaldehyde with 1-dimethylamino-3-tert-butyldimethylsiloxy butadiene catalyzed by (R,R)-1-Np-TADDOL was studied using computational methods. A theoretical rationale was developed through the combined use of molecular mechanics and ONIOM(B3LYP/6-31G(d):AM1) calculations. The origins of stereoselection in this process were identified, and excellent correlation between experiment and theory was found.

UR - http://www.scopus.com/inward/record.url?scp=51649095402&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=51649095402&partnerID=8YFLogxK

U2 - 10.1021/ol800875k

DO - 10.1021/ol800875k

M3 - Article

C2 - 18507392

AN - SCOPUS:51649095402

SN - 1523-7060

VL - 10

SP - 2749

EP - 2752

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this