Rhodium-carbenoid-mediated intermolecular O-H insertion reactions: A dramatic additive effect. Application in the synthesis of an ascomycin derivative

Todd D. Nelson; Zhiguo Jake Song; Andrew S. Thompson; Mangzhu Zhao; Anthony Demarco; Robert A. Reamer; Martha F. Huntington; Edward J.J. Grabowski; Paul J. Reider

doi:10.1016/S0040-4039(00)00069-1

Rhodium-carbenoid-mediated intermolecular O-H insertion reactions: A dramatic additive effect. Application in the synthesis of an ascomycin derivative

Todd D. Nelson, Zhiguo Jake Song, Andrew S. Thompson, Mangzhu Zhao, Anthony Demarco, Robert A. Reamer, Martha F. Huntington, Edward J.J. Grabowski, Paul J. Reider

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

42 Scopus citations

Abstract

A catalyst system of Rh₂(oct)₄/DIPEA or TMU allows for the rapid construction of α-alkoxyketones from the corresponding α-diazo ketone and alcohol. This methodology was applied to the synthesis of immunoregulant 1. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	1877-1881
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4039(00)00069-1
State	Published - Mar 18 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)00069-1

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Nelson, T. D., Song, Z. J., Thompson, A. S., Zhao, M., Demarco, A., Reamer, R. A., Huntington, M. F., Grabowski, E. J. J., & Reider, P. J. (2000). Rhodium-carbenoid-mediated intermolecular O-H insertion reactions: A dramatic additive effect. Application in the synthesis of an ascomycin derivative. Tetrahedron Letters, 41(12), 1877-1881. https://doi.org/10.1016/S0040-4039(00)00069-1

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abstract = "A catalyst system of Rh2(oct)4/DIPEA or TMU allows for the rapid construction of α-alkoxyketones from the corresponding α-diazo ketone and alcohol. This methodology was applied to the synthesis of immunoregulant 1. (C) 2000 Elsevier Science Ltd.",

author = "Nelson, {Todd D.} and Song, {Zhiguo Jake} and Thompson, {Andrew S.} and Mangzhu Zhao and Anthony Demarco and Reamer, {Robert A.} and Huntington, {Martha F.} and Grabowski, {Edward J.J.} and Reider, {Paul J.}",

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doi = "10.1016/S0040-4039(00)00069-1",

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Nelson, TD, Song, ZJ, Thompson, AS, Zhao, M, Demarco, A, Reamer, RA, Huntington, MF, Grabowski, EJJ & Reider, PJ 2000, 'Rhodium-carbenoid-mediated intermolecular O-H insertion reactions: A dramatic additive effect. Application in the synthesis of an ascomycin derivative', Tetrahedron Letters, vol. 41, no. 12, pp. 1877-1881. https://doi.org/10.1016/S0040-4039(00)00069-1

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T1 - Rhodium-carbenoid-mediated intermolecular O-H insertion reactions

T2 - A dramatic additive effect. Application in the synthesis of an ascomycin derivative

AU - Nelson, Todd D.

AU - Song, Zhiguo Jake

AU - Thompson, Andrew S.

AU - Zhao, Mangzhu

AU - Demarco, Anthony

AU - Reamer, Robert A.

AU - Huntington, Martha F.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

PY - 2000/3/18

Y1 - 2000/3/18

N2 - A catalyst system of Rh2(oct)4/DIPEA or TMU allows for the rapid construction of α-alkoxyketones from the corresponding α-diazo ketone and alcohol. This methodology was applied to the synthesis of immunoregulant 1. (C) 2000 Elsevier Science Ltd.

AB - A catalyst system of Rh2(oct)4/DIPEA or TMU allows for the rapid construction of α-alkoxyketones from the corresponding α-diazo ketone and alcohol. This methodology was applied to the synthesis of immunoregulant 1. (C) 2000 Elsevier Science Ltd.

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Rhodium-carbenoid-mediated intermolecular O-H insertion reactions: A dramatic additive effect. Application in the synthesis of an ascomycin derivative

Abstract

All Science Journal Classification (ASJC) codes

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