… control in remote asymmetric induction. Highly efficient 1, 7-asymmetric inductive hydride reduction and Grignard reaction of γ-keto esters of 1, 1′-binaphthalen-2-ols …

…, M Akiyama, K Seino, H Takayama, T Oyama…

Index: Tamai, Yasufumi; Hattori, Tetsutaro; Date, Masamitsu; Koike, Shinji; Kamikubo, Yoshinori; Akiyama, Masahiro; Seino, Kazuhiro; Takayama, Hideki; Oyama, Tomohito; Miyano, Sotaro Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 12 p. 1685 - 1694

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Abstract

Highly efficient 1, 7-asymmetric induction was achieved in DIBAL-H reduction and Grignard reaction of γ-keto esters of podand-type 1, 1′-binaphthalen-2-ol derivatives bearing an appropriate oligoether group as the 2′-substituent. Thus, the DIBAL-H reduction of keto esters 4 in dichloromethane–toluene at–78° C in the presence of an excess of MgBr2· OEt2 afforded, after further reduction of the resulting diastereomeric hydroxy esters, 1, 4-diol 8 ...