Organic Letters

, том 19 , издание 10 , страницы 2630-2633

Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols

Тип публикации: Journal Article

Дата публикации: 2017-05-03

American Chemical Society (ACS)

Organic Letters

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SJR: 1.235

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.7b00961

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PubMed ID: 28467706

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

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A vanadium catalyzed 1,3-rearrangement of allenols to form transient vanadium enolates that selectively couple with electrophilic nitrogen sources is reported even in the presence of competing simple protonation and Alder-ene pathways. Hydrazine products can be cyclized in a 6-endo-trig fashion which, upon reductive cleavage of the N-N bond, yield 1,4-diamines. Additionally, cleavage of the N-N bond before cyclization can be achieved to form β-hydroxy amines, a common structural motif of biologically active compounds.

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Trost B. M., Tracy J. S. Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols // Organic Letters. 2017. Vol. 19. No. 10. pp. 2630-2633.

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Trost B. M., Tracy J. S. Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols // Organic Letters. 2017. Vol. 19. No. 10. pp. 2630-2633.

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TY - JOUR

DO - 10.1021/acs.orglett.7b00961

UR - https://doi.org/10.1021/acs.orglett.7b00961

TI - Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols

T2 - Organic Letters

AU - Trost, Barry M.

AU - Tracy, J S

PY - 2017

DA - 2017/05/03

PB - American Chemical Society (ACS)

SP - 2630-2633

IS - 10

VL - 19

PMID - 28467706

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2017_Trost,

author = {Barry M. Trost and J S Tracy},

title = {Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols},

journal = {Organic Letters},

year = {2017},

volume = {19},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/acs.orglett.7b00961},

number = {10},

pages = {2630--2633},

doi = {10.1021/acs.orglett.7b00961}

}

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Trost, Barry M., and J S Tracy. “Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols.” Organic Letters, vol. 19, no. 10, May. 2017, pp. 2630-2633. https://doi.org/10.1021/acs.orglett.7b00961.