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2002•Journal of Synthetic Organic Chemistry JapanOpen access

Asymmetric Desymmetrization: Simultaneous Stereocontrol of Multi-chiral Centers.

Kōichi Mikami, Akihiko Yoshida

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Abstract

“Asymmetric desymmetrization” is an efficient and powerful methodology for optically active substances with complex structures. Enantiotopic group differentiation reactions starting from meso compound with chiral centers can afford chiral/non-racemic compounds bearing controlled multi-chiral centers. We introduce many useful examples of asymmetric desymmetrization, which have ever been reported, and our results on asymmetric desymmetrization using asymmetric ene reactions catalyzed by chiral BINOL-Ti complex.

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What this paper is about

“Asymmetric desymmetrization” is an efficient and powerful methodology for optically active substances with complex structures. Enantiotopic group differentiation reactions starting from meso compound with chiral centers can afford chiral/non-racemic compounds bearing controlled multi-chiral centers. We introduce many useful examples of asymmetric desymmetrization, which have ever been reported, and our results on asymmetric desymmetrization using asymmetric ene reactions catalyzed by chiral BINOL-Ti complex.

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Available abstract

“Asymmetric desymmetrization” is an efficient and powerful methodology for optically active substances with complex structures. Enantiotopic group differentiation reactions starting from meso compound with chiral centers can afford chiral/non-racemic compounds bearing controlled multi-chiral centers. We introduce many useful examples of asymmetric desymmetrization, which have ever been reported, and our results on asymmetric desymmetrization using asymmetric ene reactions catalyzed by chiral BINOL-Ti complex.

Key concepts: Desymmetrization, Enantioselective synthesis, Chemistry, Optically active, Stereochemistry, Combinatorial chemistry, Catalysis, Organic chemistry

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