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Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(O i Pr) 4
Author(s) -
Mao Jincheng,
Wan Boshun,
Wu Fan,
Lu Shiwei
Publication year - 2005
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20165
Subject(s) - chemistry , phenylacetylene , sulfamide , enantioselective synthesis , amine gas treating , sulfonamide , medicinal chemistry , catalysis , alcohol , chirality (physics) , organic chemistry , hydroamination , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Ephedrine‐derived sulfamide–amine alcohol 3 was found to be an effective catalyst for the asymmetric phenylacetylene addition to aldehydes at room temperature without using Ti(O i Pr) 4 and Zn(OTf) 2 . It afforded the propargylic alcohols in high yields (up to 99%) and good enantioselectivities (up to 84% ee), which were much higher than that based on N ‐methylephedrine under the same reaction conditions. Its weakly coordinative sulfonamide moiety of the ligand plays an important role for further acceleration and stereocontrol in the alkynylation. Chirality 17:245–249, 2005. © 2005 Wiley‐Liss, Inc.