New strategies for enantioselective syntheses of 1-alkyl-and 1, 4-dialkyl-1, 2, 3, 4-tetrahydroisoquinolines: diastereoselective additions of nucleophiles and …

GB Richter-Addo, DA Knight, MA Dewey…

Index: Richter-Addo, George B.; Knight, D. Andrew; Dewey, Michael A.; Arif, Atta M.; Gladysz Journal of the American Chemical Society, 1993 , vol. 115, # 25 p. 11863 - 11873

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Citation Number: 42

Abstract

Abstract: The chiral rhenium isoquinoline complex [(TJ~-C~ H~) R~(NO)(PP~~)(~ SO-NC~ H~)]+ TfO-(1) and (CH3) 3-SiCH2Li give the addition product (TJ~-C~ HS) R~(NO)(PP~~)(NCH= CHC (CH)~ CCHCH~ S~(CH~)~)(2) in 71% yield as a 94: 6 SS, RR/SR, RS diastereomer mixture. Similar reactions with RMgX (R=(CH3) 2CH, CHsCH2, CdHsCH2, CH~(CHZ)~, CH3, CH3 (CH2) 3) give analogous adducts (3-8) as 89-82: 11-1 ...