Chirality transferring [3,3] sigmatropic rearrangement of (1‐acyloxy‐2‐alkenyl)trialkylsilane synthesis of optically active vinylsilane‐containing α‐amino acid | Zendy

Sakaguchi Kazuhiko | Zendy; Suzuki Hiroyuki | Zendy; Ohfune Yasufumi | Zendy

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Chirality transferring [3,3] sigmatropic rearrangement of (1‐acyloxy‐2‐alkenyl)trialkylsilane synthesis of optically active vinylsilane‐containing α‐amino acid

Author(s) -

Sakaguchi Kazuhiko,

Suzuki Hiroyuki,

Ohfune Yasufumi

Publication year - 2001

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.1045

Subject(s) - chemistry , vinylsilane , chirality (physics) , optically active , stereochemistry , sigmatropic reaction , claisen rearrangement , asymmetric carbon , amino acid , axial chirality , enantioselective synthesis , organic chemistry , catalysis , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark

A vinylsilane‐containing α‐amino acid and α,α‐disubstituted α‐amino acid 2 having two contiguous asymmetric carbon centers at their α and β positions were synthesized in an optically active form by ester‐enolate Claisen rearrangement of the α‐acyloxysilane 1 as the key step, where the chirality of an α‐acyloxy‐TBDMS group was completely transferred to the rearranged product. Chirality 13:357–365, 2001. © 2001 Wiley‐Liss, Inc.

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