A syn-Selective Aza-Aldol Reaction of Boron Aza-Enolates Generated from N-Sulfonyl-1,2,3-Triazoles and 9-BBN-H

Tomoya Miura; Takayuki Nakamuro; Sho Miyakawa; Masahiro Murakami

doi:10.1002/anie.201603270

A syn-Selective Aza-Aldol Reaction of Boron Aza-Enolates Generated from N-Sulfonyl-1,2,3-Triazoles and 9-BBN-H

Tomoya Miura, Takayuki Nakamuro, Sho Miyakawa, Masahiro Murakami

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

38 Citations (Scopus)

Abstract

A syn-selective aza-aldol reaction of boron aza-enolates, generated from N-sulfonyl-1,2,3-triazoles and 9-BBN-H, is reported. It provides a sequential one-pot procedure for the stereoselective construction of 1,3-amino alcohols, having contiguous stereocenters, starting from terminal alkynes.

Original language	English
Pages (from-to)	8732-8735
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	30
DOIs	https://doi.org/10.1002/anie.201603270
Publication status	Published - Jul 18 2016
Externally published	Yes

Keywords

aldol reaction
boron
carbenoids
rhodium
triazoles

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201603270

Cite this

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title = "A syn-Selective Aza-Aldol Reaction of Boron Aza-Enolates Generated from N-Sulfonyl-1,2,3-Triazoles and 9-BBN-H",

abstract = "A syn-selective aza-aldol reaction of boron aza-enolates, generated from N-sulfonyl-1,2,3-triazoles and 9-BBN-H, is reported. It provides a sequential one-pot procedure for the stereoselective construction of 1,3-amino alcohols, having contiguous stereocenters, starting from terminal alkynes.",

keywords = "aldol reaction, boron, carbenoids, rhodium, triazoles",

author = "Tomoya Miura and Takayuki Nakamuro and Sho Miyakawa and Masahiro Murakami",

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doi = "10.1002/anie.201603270",

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AU - Miura, Tomoya

AU - Nakamuro, Takayuki

AU - Miyakawa, Sho

AU - Murakami, Masahiro

N1 - Funding Information: We thank Dr. Y. Nagata (Kyoto University) for his kind help in an X-ray analysis. This work was supported in part by Grants-in-Aid for Scientific Research (S) (15H05756) and (C) (16K05694) from MEXT. T. N. acknowledged JSPS fellowship for young scientists. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/7/18

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N2 - A syn-selective aza-aldol reaction of boron aza-enolates, generated from N-sulfonyl-1,2,3-triazoles and 9-BBN-H, is reported. It provides a sequential one-pot procedure for the stereoselective construction of 1,3-amino alcohols, having contiguous stereocenters, starting from terminal alkynes.

AB - A syn-selective aza-aldol reaction of boron aza-enolates, generated from N-sulfonyl-1,2,3-triazoles and 9-BBN-H, is reported. It provides a sequential one-pot procedure for the stereoselective construction of 1,3-amino alcohols, having contiguous stereocenters, starting from terminal alkynes.

KW - aldol reaction

KW - boron

KW - carbenoids

KW - rhodium

KW - triazoles

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A syn-Selective Aza-Aldol Reaction of Boron Aza-Enolates Generated from N-Sulfonyl-1,2,3-Triazoles and 9-BBN-H

Abstract

Keywords

ASJC Scopus subject areas

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