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Enantioselective Platinum‐Catalyzed Silicon‐Boron Addition to 1,3‐Cyclohexadiene
Author(s) -
Gerdin Martin,
Moberg Christina
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505016
Subject(s) - chemistry , enantioselective synthesis , phosphoramidite , catalysis , boron , platinum , cyclohexene , silicon , medicinal chemistry , organic chemistry , dna , biochemistry , oligonucleotide
Silaboration of 1,3‐cyclohexadiene in the presence of Pt(acac) 2 , DIBALH, and a phosphoramidite prepared from ( S )‐1,1′‐bi‐2‐naphthol and diisopropylamine led to (1 R ,4 S )‐1‐(dimethylphenylsilyl)‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐2‐cyclohexene with 70% ee. Chiral catalysts based on Ni gave no or essentially racemic product, whereas complexes containing Pd were inactive.