Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: Application in the synthesis of apple leafminer pheromones

Chemical Communications

Volumn , Issue 11, 2005, Pages 1387-1389

  Van Summeren, Ruben P ^a   Reijmer, Sven J W ^a   Feringa, Ben L ^a   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ISOPRENOID; NATURAL PRODUCT; PHEROMONE; RUTHENIUM; ZIRCONIUM;

APPLE; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 16444368600     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b419268k     Document Type: Article

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23. Partial racemization of the cis-adduct 5b upon use of TMSOTf is probably due to the fact that TMSOTf is reactive enough to convert small quantities of (meso) ketone into racemic 5b while TMSC1 is not.
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29. 4 and a smaller excess of Grignard reagent (5 eq.) was less successful, with incomplete reaction after 12 h and partial exchange of the tosyl group by bromide.
30. 12 was not separated from dodecane, which resulted from homocoupling of the Grignard. The estimated yield (GC) of 12 was 70%.