PMID- 18557644
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20080926
LR  - 20080711
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 73
IP  - 14
DP  - 2008 Jul 18
TI  - Heterocyclic lithium amides as chiral ligands for an enantioselective 
      hydroxyalkylation with n-BuLi.
PG  - 5397-409
LID - 10.1021/jo8005396 [doi]
AB  - Chiral heterocyclic structures based on 3-aminopyrrolidines (3APs), 
      3-aminotetrahydrothiophens (3ATTs), and 3-aminotetrahydrofurans (3ATFs) have been 
      synthesized. The corresponding lithium amides have been evaluated as chiral 
      ligands in the condensation of n-BuLi on o-tolualdehyde. The returned levels of 
      induction were in the 46-80% ee range. The cheap and easily prepared 3ATFLi's 
      turned out to be also the best ligands, giving access to the expected R or S 
      alcohols in a same 80% level of induction at -78 degrees C in THF. In all cases, 
      the sense of induction depends on the absolute configuration of C(8) on the 
      3-amino appendage. A general concept is proposed to rationalize the process of 
      induction in the presence of organolithium species.
FAU - Duguet, Nicolas
AU  - Duguet N
AD  - Laboratoire des Fonctions Azotees & Oxygenees Complexes de l'IRCOF, UMR CNRS 
      6014, Universite de Rouen and INSA de Rouen, 76821 Mont St Aignan Cedex, France.
FAU - Petit, Sylvain M
AU  - Petit SM
FAU - Marchand, Philippe
AU  - Marchand P
FAU - Harrison-Marchand, Anne
AU  - Harrison-Marchand A
FAU - Maddaluno, Jacques
AU  - Maddaluno J
LA  - eng
PT  - Journal Article
DEP - 20080617
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
EDAT- 2008/06/19 09:00
MHDA- 2008/06/19 09:01
CRDT- 2008/06/19 09:00
PHST- 2008/06/19 09:00 [pubmed]
PHST- 2008/06/19 09:01 [medline]
PHST- 2008/06/19 09:00 [entrez]
AID - 10.1021/jo8005396 [doi]
PST - ppublish
SO  - J Org Chem. 2008 Jul 18;73(14):5397-409. doi: 10.1021/jo8005396. Epub 2008 Jun 
      17.