Chemistry of planar chiral medium-sized heterocycles

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Abstract

Nine-membered E,Z-diallylic heterocycles 1 and [7]-orthocyclphenes 2 exhibit planar chirality at ambient temperature. Their stereochemical stabilities are highly dependent on substituent R1 on the E-Alkene, embedded heteroatom X in the ring, and ring size. Their planar chirality can be transformed into carbon central chirality without loss of enantiopurity. Therefore, they are useful chiral building blocks for biologically active chiral molecules and precursors for chiral reagents. The enantioenriched forms of 1 and 2 are available by optical resolution of racemate, and asymmetric synthesis based on enantioselective cyclization. Planar chiral dialkoxysilane 32 and ketone 33 were also developed.

Original languageEnglish
Pages (from-to)449-457
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume75
Issue number5
DOIs
Publication statusPublished - Jan 1 2017

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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