PMID- 16209582
OWN - NLM
STAT- MEDLINE
DCOM- 20060628
LR  - 20051007
IS  - 0022-3263 (Print)
IS  - 0022-3263 (Linking)
VI  - 70
IP  - 21
DP  - 2005 Oct 14
TI  - Stereoselective formation of carbon-carbon bonds via SN2-displacement: synthesis 
      of substituted cycloalkyl[b]indoles.
PG  - 8385-94
AB  - A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been 
      accomplished. The key features of this approach are (1) the utilization of a 
      Japp-Klingemann condensation/Fischer cyclization to prepare 
      cycloalkyl[b]indolones, (2) the asymmetric borane reduction of these heterocyclic 
      ketones with (S)-OAB to obtain enantiomerically pure alcohols, and (3) the 
      stereoselective S(N)2-displacement of these indole alcohol substrates with a 
      carbon nucleophile under Mitsunobu conditions to set the C1 or C3 tertiary carbon 
      stereocenter. The use of trimethylphosphine (PMe3) and bis(2,2,2-trichloroethyl) 
      azodicarboxylate (TCEAD) was found to have an effect on the Mitsunobu dehydrative 
      alkylation.
FAU - Hillier, Michael C
AU  - Hillier MC
AD  - Department of Process Research, Merck and Company, P.O. Box 2000, Rahway, New 
      Jersey 07065, USA. michael_hillier@merck.com
FAU - Marcoux, Jean-Francois
AU  - Marcoux JF
FAU - Zhao, Dalian
AU  - Zhao D
FAU - Grabowski, Edward J J
AU  - Grabowski EJ
FAU - McKeown, Arlene E
AU  - McKeown AE
FAU - Tillyer, Richard D
AU  - Tillyer RD
LA  - eng
PT  - Journal Article
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
RN  - 0 (Indoles)
RN  - 7440-44-0 (Carbon)
SB  - IM
MH  - Carbon/*chemistry
MH  - Cyclization
MH  - Indoles/*chemical synthesis/chemistry
MH  - Molecular Structure
MH  - Stereoisomerism
EDAT- 2005/10/08 09:00
MHDA- 2006/06/29 09:00
CRDT- 2005/10/08 09:00
PHST- 2005/10/08 09:00 [pubmed]
PHST- 2006/06/29 09:00 [medline]
PHST- 2005/10/08 09:00 [entrez]
AID - 10.1021/jo051146p [doi]
PST - ppublish
SO  - J Org Chem. 2005 Oct 14;70(21):8385-94. doi: 10.1021/jo051146p.