- Synthesis of (3S)-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one as a key intermediate of sphingosine 1-phosphate-1 receptor agonists
-
Herein we report the asymmetric synthesis of (3S)-(tert- butyldimethylsilyloxy)methylcyclopentan-1-one (S)-3 as a practical chiral synthon for a wide range of pharmaceutical and/or natural products, using Lipshutz's asymmetric copper-catalyzed conjugate reduction. This method makes it feasible to prepare a conformationally constrained cyclopentane analogue 12, which is one of the key intermediates for the synthesis of novel sphingosine 1-phosphate-1 receptor agonists.
- Asano, Masayoshi,Nakamura, Tsuyoshi,Sekiguchi, Yukiko,Mizuno, Yumiko,Yamaguchi, Takahiro,Kuroda, Takeshi,Tamaki, Kazuhiko,Nishi, Takahide
-
p. 449 - 456
(2013/07/11)
-
- Synthesis of D- And L-carbocyclic nucleosides via rhodium-catalyzed asymmetric hydroacylation as the key step
-
(Chemical Equation Presented) D- and L-carbocyclic nucleosides were obtained by a new procedure involving an enantioselective rhodium/duphos- catalyzed hydroacylation reaction as the key step. The 3-hydroxymethyl- cyclopentanol intermediate was obtained by stereoselective reduction of ketone and by dynamic kinetic resolution (DKR).
- Marce, Patricia,Diaz, Yolanda,Matheu, M. Isabel,Castillon, Sergio
-
supporting information; experimental part
p. 4735 - 4738
(2009/05/31)
-
- Photo-induced intermolecular radical β-addition to chiral α- (arylsulfinyl) enones
-
The reactions of α-(arylsulfinyl) enones with alkyl radicals having a hydroxy or acetal group were examined under photo-irradiation in the presence of benzophenone. High diastereoselectivity was observed in the photo-induced radical reaction of 2-(arylsulfinyl)-2-cyclopentenones having a bulky aryl group, such as the 2,4,6-triisopropylphenyl or 2,4, 6-trimethylphenyl group. The photo-induced reaction of 3-[(2,4,6-triisopropylphenyl)sulfinyl]-3- pentene-2-one in 1,3-dioxolane also gave a single diastereomer of the 1,3- dioxolan-2-yl adduct.
- Mase, Nobuyuki
-
p. 2957 - 2965
(2007/10/03)
-
- ASYMMETRIC CONJUGATE ADDITIONS OF AN HYDROXYMETHYL CARBANION EQUIVALENT. SYNTHESIS OF (+)-A FACTOR
-
An effective procedure is presented for generation of Ph2CH2OCH2Li via tin -> lithium exchange and for conjugate addition of this HOCH2- equivalent to some homochiral cycloalkenone and butenolide sulfoxides.
- Posner, Gary H.,Weitzberg, Moshe,Jew, Sang-sup
-
p. 611 - 620
(2007/10/02)
-
