Enantioselective C-C bond cleavage creating chiral quaternary carbon centers

Takanori Matsuda; Masanori Shigeno; Masaomi Makino; Masahiro Murakami

doi:10.1021/ol061359g

Enantioselective C-C bond cleavage creating chiral quaternary carbon centers

Takanori Matsuda, Masanori Shigeno, Masaomi Makino, Masahiro Murakami

PHA - Molecular Pharmaceutical Science

Kyoto University

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

127 Citations (Scopus)

Abstract

A chiral all-carbon benzylic quaternary carbon center is created by the asymmetric intramolecular addition/ring-opening reaction of a boryl-substituted cyclobutanone, which involves enantioselective β-carbon elimination from a symmetrical rhodium cyclobutanolate. The asymmetric reaction was successfully applied to a synthesis of sesquiterpene, (-)-α-herbertenol.

Original language	English
Pages (from-to)	3379-3381
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	15
DOIs	https://doi.org/10.1021/ol061359g
Publication status	Published - 2006 Jul 20

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10.1021/ol061359g

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abstract = "A chiral all-carbon benzylic quaternary carbon center is created by the asymmetric intramolecular addition/ring-opening reaction of a boryl-substituted cyclobutanone, which involves enantioselective β-carbon elimination from a symmetrical rhodium cyclobutanolate. The asymmetric reaction was successfully applied to a synthesis of sesquiterpene, (-)-α-herbertenol.",

author = "Takanori Matsuda and Masanori Shigeno and Masaomi Makino and Masahiro Murakami",

year = "2006",

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AU - Matsuda, Takanori

AU - Shigeno, Masanori

AU - Makino, Masaomi

AU - Murakami, Masahiro

PY - 2006/7/20

Y1 - 2006/7/20

N2 - A chiral all-carbon benzylic quaternary carbon center is created by the asymmetric intramolecular addition/ring-opening reaction of a boryl-substituted cyclobutanone, which involves enantioselective β-carbon elimination from a symmetrical rhodium cyclobutanolate. The asymmetric reaction was successfully applied to a synthesis of sesquiterpene, (-)-α-herbertenol.

AB - A chiral all-carbon benzylic quaternary carbon center is created by the asymmetric intramolecular addition/ring-opening reaction of a boryl-substituted cyclobutanone, which involves enantioselective β-carbon elimination from a symmetrical rhodium cyclobutanolate. The asymmetric reaction was successfully applied to a synthesis of sesquiterpene, (-)-α-herbertenol.

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Enantioselective C-C bond cleavage creating chiral quaternary carbon centers

Abstract

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