Ab initio study of endo/exo and diastereofacial selectivities in Diels-Alder reactions between chiral butenolides and cyclopentadiene

Abdelouahid Sbai; Vicenç Branchadell; Antonio Oliva

Ab initio study of endo/exo and diastereofacial selectivities in Diels-Alder reactions between chiral butenolides and cyclopentadiene

Abdelouahid Sbai, Vicenç Branchadell, Antonio Oliva

Department of Chemistry

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

19 Citations (Scopus)

Abstract

Diels-Alder reactions of cyclopentadiene with crotonolactone and β-angelica lactone have been studied using ab initio methods at the MP3/6-31G*//RHF/3-21G and MP2/6-31G*//RHF/6-31G* levels. The transition states corresponding to the formation of different stereoisomers and diastereoisomers have been located. The results obtained show that the correct endo/exo selectivity is only obtained when polarization functions are included in the basis set. However, syn/anti selectivity is correctly described at all levels of calculation.

Original language	English
Pages (from-to)	621-626
Journal	Journal of Organic Chemistry
Volume	61
Issue number	2
Publication status	Published - 26 Jan 1996

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@article{90482fd7866b4489bd317f32d6589d55,

title = "Ab initio study of endo/exo and diastereofacial selectivities in Diels-Alder reactions between chiral butenolides and cyclopentadiene",

abstract = "Diels-Alder reactions of cyclopentadiene with crotonolactone and β-angelica lactone have been studied using ab initio methods at the MP3/6-31G*//RHF/3-21G and MP2/6-31G*//RHF/6-31G* levels. The transition states corresponding to the formation of different stereoisomers and diastereoisomers have been located. The results obtained show that the correct endo/exo selectivity is only obtained when polarization functions are included in the basis set. However, syn/anti selectivity is correctly described at all levels of calculation.",

author = "Abdelouahid Sbai and Vicen{\c c} Branchadell and Antonio Oliva",

year = "1996",

month = jan,

day = "26",

language = "English",

volume = "61",

pages = "621--626",

number = "2",

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TY - JOUR

T1 - Ab initio study of endo/exo and diastereofacial selectivities in Diels-Alder reactions between chiral butenolides and cyclopentadiene

AU - Sbai, Abdelouahid

AU - Branchadell, Vicenç

AU - Oliva, Antonio

PY - 1996/1/26

Y1 - 1996/1/26

N2 - Diels-Alder reactions of cyclopentadiene with crotonolactone and β-angelica lactone have been studied using ab initio methods at the MP3/6-31G*//RHF/3-21G and MP2/6-31G*//RHF/6-31G* levels. The transition states corresponding to the formation of different stereoisomers and diastereoisomers have been located. The results obtained show that the correct endo/exo selectivity is only obtained when polarization functions are included in the basis set. However, syn/anti selectivity is correctly described at all levels of calculation.

AB - Diels-Alder reactions of cyclopentadiene with crotonolactone and β-angelica lactone have been studied using ab initio methods at the MP3/6-31G*//RHF/3-21G and MP2/6-31G*//RHF/6-31G* levels. The transition states corresponding to the formation of different stereoisomers and diastereoisomers have been located. The results obtained show that the correct endo/exo selectivity is only obtained when polarization functions are included in the basis set. However, syn/anti selectivity is correctly described at all levels of calculation.

M3 - Article

VL - 61

SP - 621

EP - 626

IS - 2

ER -