On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds. 1. Rotational profiles of propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3.

G. Frenking; K. F. Köhler; M. T. Reetz

doi:10.1016/S0040-4020(01)86504-2

On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds. 1. Rotational profiles of propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3.

G. Frenking, K. F. Köhler, M. T. Reetz

University of Marburg

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

44 Scopus citations

Abstract

The conformational profiles for rotation around the CC(O) bond α and the energy minimum conformations are calculated for propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3 at MP2/6-31G(d)//HF/6-31G(d). The energy level of the LUMO is calculated as a function of α for 1, 2, and 3 and discussed in relationship to the Felkin-Anh model.

Original language	English
Pages (from-to)	8991-9004
Number of pages	14
Journal	Tetrahedron
Volume	47
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4020(01)86504-2
State	Published - 4 Nov 1991
Externally published	Yes

Access to Document

10.1016/S0040-4020(01)86504-2

Cite this

@article{ec4d8bc129c2499f90192bb92be472ce,

title = "On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds. 1. Rotational profiles of propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3.",

abstract = "The conformational profiles for rotation around the CC(O) bond α and the energy minimum conformations are calculated for propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3 at MP2/6-31G(d)//HF/6-31G(d). The energy level of the LUMO is calculated as a function of α for 1, 2, and 3 and discussed in relationship to the Felkin-Anh model.",

author = "G. Frenking and K{\"o}hler, {K. F.} and Reetz, {M. T.}",

year = "1991",

month = nov,

day = "4",

doi = "10.1016/S0040-4020(01)86504-2",

language = "英语",

volume = "47",

pages = "8991--9004",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "43",

}

On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds. 1. Rotational profiles of propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3. / Frenking, G.; Köhler, K. F.; Reetz, M. T.
In: Tetrahedron, Vol. 47, No. 43, 04.11.1991, p. 8991-9004.

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

TY - JOUR

T1 - On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds. 1. Rotational profiles of propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3.

AU - Frenking, G.

AU - Köhler, K. F.

AU - Reetz, M. T.

PY - 1991/11/4

Y1 - 1991/11/4

N2 - The conformational profiles for rotation around the CC(O) bond α and the energy minimum conformations are calculated for propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3 at MP2/6-31G(d)//HF/6-31G(d). The energy level of the LUMO is calculated as a function of α for 1, 2, and 3 and discussed in relationship to the Felkin-Anh model.

AB - The conformational profiles for rotation around the CC(O) bond α and the energy minimum conformations are calculated for propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3 at MP2/6-31G(d)//HF/6-31G(d). The energy level of the LUMO is calculated as a function of α for 1, 2, and 3 and discussed in relationship to the Felkin-Anh model.

UR - http://www.scopus.com/inward/record.url?scp=0026076172&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)86504-2

DO - 10.1016/S0040-4020(01)86504-2

M3 - 文章

AN - SCOPUS:0026076172

SN - 0040-4020

VL - 47

SP - 8991

EP - 9004

JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds. 1. Rotational profiles of propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3.

Abstract

Access to Document

Other files and links

Fingerprint

Cite this