Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction

S. M. Moharram; G. Hirai; K. Koyama; H. Oguri; M. Hirama

doi:10.1016/S0040-4039(00)01116-3

Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction

S. M. Moharram, G. Hirai, K. Koyama, H. Oguri, M. Hirama

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

13 Citations (Scopus)

Abstract

The presence of molecular sieves 4Å (MS 4Å) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4Å the (R)-adduct was formed in 72% ee, and in the presence of MS 4Å the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4Å has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6669-6673
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(00)01116-3
Publication status	Published - Aug 19 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)01116-3

Cite this

@article{4faea9603f084da08b53e9f26fed67fd,

title = "Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction",

abstract = "The presence of molecular sieves 4{\AA} (MS 4{\AA}) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4{\AA} the (R)-adduct was formed in 72% ee, and in the presence of MS 4{\AA} the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4{\AA} has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd.",

author = "Moharram, {S. M.} and G. Hirai and K. Koyama and H. Oguri and M. Hirama",

note = "Funding Information: We are grateful to Professor Nobuyuki Harada and Dr. Chizuko Kabuto for their assistance in X-ray analysis. A postdoctoral fellowship from the Japanese Society for the Promotion of Science (S.M.M.) is gratefully acknowledged. This study was supported financially in part by Suntory Institute for Bioorganic Research. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

year = "2000",

month = aug,

day = "19",

doi = "10.1016/S0040-4039(00)01116-3",

language = "English",

volume = "41",

pages = "6669--6673",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "34",

}

TY - JOUR

T1 - Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction

AU - Moharram, S. M.

AU - Hirai, G.

AU - Koyama, K.

AU - Oguri, H.

AU - Hirama, M.

N1 - Funding Information: We are grateful to Professor Nobuyuki Harada and Dr. Chizuko Kabuto for their assistance in X-ray analysis. A postdoctoral fellowship from the Japanese Society for the Promotion of Science (S.M.M.) is gratefully acknowledged. This study was supported financially in part by Suntory Institute for Bioorganic Research. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2000/8/19

Y1 - 2000/8/19

N2 - The presence of molecular sieves 4Å (MS 4Å) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4Å the (R)-adduct was formed in 72% ee, and in the presence of MS 4Å the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4Å has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd.

AB - The presence of molecular sieves 4Å (MS 4Å) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4Å the (R)-adduct was formed in 72% ee, and in the presence of MS 4Å the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4Å has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd.

UR - http://www.scopus.com/inward/record.url?scp=0034686868&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034686868&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)01116-3

DO - 10.1016/S0040-4039(00)01116-3

M3 - Article

AN - SCOPUS:0034686868

SN - 0040-4039

VL - 41

SP - 6669

EP - 6673

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this