Stereochemistry in Asymmetric Alkylation of Aldimine via Chiral Bis(oxazolyl)phenylplatinum Complexes

Chiral (S,S)-(Phebox)PtCl complex 2 [Phebox = bis(oxazolyl)phenyl] and its cationic complexes (Phebox)Pt(OTf) (3) and [(Phebox)Pt(H2O)](BF4) (4) were synthesized by the transmetalation reaction of (Phebox)SnMe3 (1) with K[PtCl3(C2H4)](H2O) and subsequent treatment with silver salts. Both cationic co...

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Published inOrganometallics Vol. 18; no. 18; pp. 3584 - 3588
Main Authors Motoyama, Yukihiro, Mikami, Yoshiharu, Kawakami, Hidekazu, Aoki, Katsuyuki, Nishiyama, Hisao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.08.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
COPPER(II) COMPLEXES
METHYL ISOCYANOACETATE
LEWIS-ACID
ALDOL REACTION
CRYSTAL-STRUCTURE
DIELS-ALDER REACTION
ENANTIOSELECTIVE ALKYLATION
ALDEHYDES
ADDITIONS
ALPHA-IMINO ESTERS
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Summary:Chiral (S,S)-(Phebox)PtCl complex 2 [Phebox = bis(oxazolyl)phenyl] and its cationic complexes (Phebox)Pt(OTf) (3) and [(Phebox)Pt(H2O)](BF4) (4) were synthesized by the transmetalation reaction of (Phebox)SnMe3 (1) with K[PtCl3(C2H4)](H2O) and subsequent treatment with silver salts. Both cationic complexes 3 and 4 readily reacted with N-phenylbenzaldimine (7) to afford the corresponding chiral aldimine complexes [(Phebox)Pt(aldimine)](X) (8, X = OTf; 9, X = BF4), which were subjected to alkylation with organolithium reagents resulting in 82% ee of the product amine (S)-10b.
Bibliography:ark:/67375/TPS-NQ6S4PW7-X
istex:7F5FACD88060D54F238533A19AC369491F5826C5
ISSN:0276-7333
1520-6041
DOI:10.1021/om990251k