PMID- 16402397
OWN - NLM
STAT- MEDLINE
DCOM- 20060628
LR  - 20131121
IS  - 0947-6539 (Print)
IS  - 0947-6539 (Linking)
VI  - 12
IP  - 8
DP  - 2006 Mar 1
TI  - S,O-acetals as novel "chiral aldehyde" equivalents.
PG  - 2171-87
AB  - Palladium-catalyzed asymmetric allylic alkylations (AAA) to form "chiral 
      aldehyde" equivalents were investigated. Alpha-acetoxysulfones were formed in 
      high enantiomeric excess as single regioisomers in AAA reactions of allylic 
      geminal dicarboxylates with sodium benzenesulfinate. The directing ability of 
      this novel functional group was highlighted by a series of dihydroxylations, 
      affording syn diols exclusively anti to the acetoxy sulfone as single 
      diastereomers in excellent yields. This is the first example of an asymmetric 
      dihydroxylation protocol that gives the equivalent of reaction with a simple 
      enal. The synthetic value of this process was exemplified by subsequent 
      transformations of the diols including the development of a one-pot 
      dihydroxylation-deprotective acyl migration protocol to give differentially 
      protected 1,2-diols.
FAU - Trost, Barry M
AU  - Trost BM
AD  - Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. 
      bmtrost@stanford.edu
FAU - Crawley, Matthew L
AU  - Crawley ML
FAU - Lee, Chul Bom
AU  - Lee CB
LA  - eng
GR  - GM-13598/GM/NIGMS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
RN  - 0 (Acetals)
RN  - 0 (Aldehydes)
RN  - 0 (Sulfinic Acids)
RN  - 0 (Sulfones)
RN  - 5TWQ1V240M (Palladium)
RN  - 618-41-7 (benzenesulfinic acid)
SB  - IM
MH  - Acetals/*chemistry
MH  - Aldehydes/chemistry
MH  - Alkylation
MH  - Catalysis
MH  - Hydroxylation
MH  - Molecular Conformation
MH  - Palladium/chemistry
MH  - Stereoisomerism
MH  - Sulfinic Acids/chemistry
MH  - Sulfones/chemistry
EDAT- 2006/01/13 09:00
MHDA- 2006/06/29 09:00
CRDT- 2006/01/13 09:00
PHST- 2006/01/13 09:00 [pubmed]
PHST- 2006/06/29 09:00 [medline]
PHST- 2006/01/13 09:00 [entrez]
AID - 10.1002/chem.200500919 [doi]
PST - ppublish
SO  - Chemistry. 2006 Mar 1;12(8):2171-87. doi: 10.1002/chem.200500919.