Organic Letters

, том 3 , издание 22 , страницы 3579-3582

Unexpected endo Selectivity of Conjugate Nucleophilic Addition to an Arene−Cr(CO)₃ Complex: Enantioselective Synthesis of the Diterpene 11-epi-Helioporin B

Тип публикации: Journal Article

Дата публикации: 2001-09-22

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

БС1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/ol016699a

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PubMed ID: 11678713

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

Starting from a nonracemic planar−chiral arene tricarbonyl chromium complex, an epimer of the bioactive marine diterpene helioporin B was synthesized in a highly stereoselective fashion. The stereostructure of the product (11-epi-helioporin B) corresponds to that of other serrulatane-type natural products. In a key step of the synthesis, 2-lithioacetonitrile undergoes conjugate nucleophilic addition to an unsaturated complex. Remarkably, this addition occurs in an endo mode, i.e., from the complexed face of the π-ligand.

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Dehmel F., Schmalz H. Unexpected endo Selectivity of Conjugate Nucleophilic Addition to an Arene−Cr(CO)3 Complex: Enantioselective Synthesis of the Diterpene 11-epi-Helioporin B // Organic Letters. 2001. Vol. 3. No. 22. pp. 3579-3582.

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TY - JOUR

DO - 10.1021/ol016699a

UR - https://doi.org/10.1021/ol016699a

TI - Unexpected endo Selectivity of Conjugate Nucleophilic Addition to an Arene−Cr(CO)3 Complex: Enantioselective Synthesis of the Diterpene 11-epi-Helioporin B

T2 - Organic Letters

AU - Dehmel, Florian

AU - Schmalz, H.-G.

PY - 2001

DA - 2001/09/22

PB - American Chemical Society (ACS)

SP - 3579-3582

IS - 22

VL - 3

PMID - 11678713

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2001_Dehmel,

author = {Florian Dehmel and H.-G. Schmalz},

title = {Unexpected endo Selectivity of Conjugate Nucleophilic Addition to an Arene−Cr(CO)3 Complex: Enantioselective Synthesis of the Diterpene 11-epi-Helioporin B},

journal = {Organic Letters},

year = {2001},

volume = {3},

publisher = {American Chemical Society (ACS)},

month = {sep},

url = {https://doi.org/10.1021/ol016699a},

number = {22},

pages = {3579--3582},

doi = {10.1021/ol016699a}

}

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Dehmel, Florian, and H.-G. Schmalz. “Unexpected endo Selectivity of Conjugate Nucleophilic Addition to an Arene−Cr(CO)3 Complex: Enantioselective Synthesis of the Diterpene 11-epi-Helioporin B.” Organic Letters, vol. 3, no. 22, Sep. 2001, pp. 3579-3582. https://doi.org/10.1021/ol016699a.

Издатель

American Chemical Society (ACS)

Журнал

Organic Letters

scimago Q1

wos Q1

БС1

SJR

1.235

CiteScore

8.7

Impact factor

ISSN

15237060 (Print)

15237052 (Electronic)