Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(O  i  Pr) 4 | Zendy

Mao Jincheng | Zendy; Wan Boshun | Zendy; Wu Fan | Zendy; Lu Shiwei | Zendy

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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.

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