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

43 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

Cite this

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

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

TY - JOUR

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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DO - 10.1016/S0040-4039(00)00069-1

M3 - Article

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SN - 0040-4039

VL - 41

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JO - Tetrahedron Letters

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IS - 12

ER -

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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