PMID- 21898621
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20120105
LR  - 20111005
IS  - 1521-3765 (Electronic)
IS  - 0947-6539 (Linking)
VI  - 17
IP  - 42
DP  - 2011 Oct 10
TI  - BINAP versus BINAP(O) in asymmetric intermolecular Mizoroki-Heck reactions: 
      substantial effects on selectivities.
PG  - 11914-8
LID - 10.1002/chem.201101695 [doi]
AB  - 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) was employed as chiral ligand 
      in the enantioselective intermolecular Mizoroki-Heck reaction, whereas the use of 
      cognate BINAP(O) (monooxidized BINAP) is unprecedented. The regio- and 
      enantioselectivity of the arylation of representative cyclic alkenes changes 
      dramatically in the presence of hemilabile BINAP(O) instead of BINAP. The 
      arylation of 2,3-dihydrofuran is perfectly regiodivergent (98:2 versus 0:100) and 
      the arylation of cyclopentene is only enantioselective with BINAP(O) [60 versus 
      10% enantiomeric excess (ee)]. Use of [Pd(2)(dba)(3)]⋅dba 
      (dba=dibenzylideneacetone) instead of Pd(OAc)(2) produces as high as 86% ee in 
      the arylation of cyclopentene.
CI  - Copyright (c) 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Woste, Thorsten H
AU  - Woste TH
AD  - Organisch-Chemisches Institut, Westfalische Wilhelms-Universitat Munster, 
      Corrensstrasse 40, 48149 Munster, Germany.
FAU - Oestreich, Martin
AU  - Oestreich M
LA  - eng
PT  - Journal Article
DEP - 20110906
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
EDAT- 2011/09/08 06:00
MHDA- 2011/09/08 06:01
CRDT- 2011/09/08 06:00
PHST- 2011/06/03 00:00 [received]
PHST- 2011/09/08 06:00 [entrez]
PHST- 2011/09/08 06:00 [pubmed]
PHST- 2011/09/08 06:01 [medline]
AID - 10.1002/chem.201101695 [doi]
PST - ppublish
SO  - Chemistry. 2011 Oct 10;17(42):11914-8. doi: 10.1002/chem.201101695. Epub 2011 Sep 
      6.