Reference

Pd(II)-Catalyzed Asymmetric Addition of Malonates to Dihydroisoquinolines

All Rights Reserved. Several substances are used for example 137219-86-4 which is its cas registry number. Pd(II)-Catalyzed Asymmetric Addition of Malonates to Dihydroisoquinolines. Sasamoto, Naoki; Dubs, Christian; Hamashima, Yoshitaka; Sodeoka, Mikiko (IMRAM, Tohoku University, Miyagi 980-8577, Japan). Journal of the American Chemical Society, 128(43), 14010-14011 (English) 2006 American Chemical Society. CODEN: JACSAT. ISSN: 0002-7863. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) A highly efficient reaction for catalytic asym. addn. of malonates CH2(CO2R1) (R1 = Et, Me2CH) to dihydroisoquinolines I (R2, R3, R5 = H, MeO; R3R4 = OCH2O; R4 = H, Br, Me, MeO) using chiral Pd(II) complexes in the presence of Boc2O (Boc = Me3COCO) has been developed. The substrates with various substitution patterns were available, and the reactions were complete within several hours (<3 h in most cases) under mild reaction conditions affording various optically active C1-substituted tetrahydroisoquinolines II (up to 98% yield and up to 97% ee). Furthermore, slow addn. of DDQ allowed the in situ generation of the reactive intermediate from the corresponding N-Boc-protected amine, and dehydrogenative addn. reaction was successfully demonstrated. .