PMID- 11575778
OWN - NLM
STAT- MEDLINE
DCOM- 20020122
LR  - 20190921
IS  - 0947-6539 (Print)
IS  - 0947-6539 (Linking)
VI  - 7
IP  - 17
DP  - 2001 Sep 3
TI  - AAA in KAT/DYKAT processes: first- and second-generation asymmetric syntheses of 
      (+)- and (-)-cyclophellitol.
PG  - 3768-75
AB  - Kinetic resolutions and kinetic asymmetric transformations (KAT) as well as 
      dynamic kinetic resolutions and dynamic kinetic asymmetric transformations 
      (DYKAT) are important synthetic protocols. The feasibility of KAT and DYKAT 
      processes for asymmetric allylic alkylations (AAA) is explored utilizing a single 
      substrate--conduritol B tetraesters. Both processes can be performed resulting in 
      excellent enantioselectivity. The impact of nucleophile and leaving group on the 
      effectiveness of each is outlined. The ability to differentiate the various 
      hydroxyl groups is also described. For this purpose, 
      4-tert-butyldimethylsiloxy-2,2-dimethylbutyric acid was developed as a 
      nucleophile. The utility of effecting KAT/DYKAT processes through the 
      Pd-catalyzed AAA reaction is demonstrated by efficient syntheses of both 
      enantiomers of the potent glycosidase inhibitor cyclophellitol.
FAU - Trost, B M
AU  - Trost BM
AD  - Department of Chemistry, Stanford University, CA 94305-5080, USA. 
      bmtrost@stanford.edu
FAU - Patterson, D E
AU  - Patterson DE
FAU - Hembre, E J
AU  - Hembre EJ
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PT  - Research Support, U.S. Gov't, Non-P.H.S.
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
RN  - 0 (Anti-HIV Agents)
RN  - 0 (Cyclohexanols)
RN  - 0 (Enzyme Inhibitors)
RN  - 126661-83-4 (cyclophellitol)
RN  - 7440-15-5 (Rhenium)
RN  - EC 3.2.1.21 (beta-Glucosidase)
SB  - IM
MH  - Agaricales/chemistry
MH  - Anti-HIV Agents/chemical synthesis/chemistry
MH  - Catalysis
MH  - Cyclohexanols/*chemical synthesis/chemistry
MH  - Enzyme Inhibitors/*chemical synthesis/chemistry
MH  - Methods
MH  - Rhenium/chemistry
MH  - Stereoisomerism
MH  - beta-Glucosidase/antagonists & inhibitors
EDAT- 2001/09/29 10:00
MHDA- 2002/01/23 10:01
CRDT- 2001/09/29 10:00
PHST- 2001/09/29 10:00 [pubmed]
PHST- 2002/01/23 10:01 [medline]
PHST- 2001/09/29 10:00 [entrez]
AID - 10.1002/1521-3765(20010903)7:17<3768::AID-CHEM3768>3.0.CO;2-C [pii]
AID - 10.1002/1521-3765(20010903)7:17<3768::aid-chem3768>3.0.co;2-c [doi]
PST - ppublish
SO  - Chemistry. 2001 Sep 3;7(17):3768-75. doi: 
      10.1002/1521-3765(20010903)7:17<3768::aid-chem3768>3.0.co;2-c.