126177-95-5Relevant articles and documents
Copper(II) chloride mediated racemization-free hydrolysis of α- alkylated ketone SAMP-hydrazones
Enders, Dieter,Hundertmark, Thomas,Lazny, Ryszard
, p. 27 - 33 (1999)
Treatment of ketone SAMP-hydrazones 1a-k with an aqueous copper(II) chloride solution yields the corresponding ketones 2a-k in 52-94% yield and with high enantiomeric purities (ee = 89-99%). The cleavage conditions do not affect functionalities sensitive to oxidation and strong acids. The alkylation/cleavage protocol can be carried out in 'one-pot'.
Asymmetric synthesis of 2-amino-1,3-diols and D-erythro-sphinganine
Enders, Dieter,Mueller-Huewen, Anke
, p. 1732 - 1739 (2007/10/03)
The asymmetric synthesis of protected 2-amino-1,3-diols (S,R)-5 starting from 2,2-dimethyl-1,3-dioxan-5-one is described. The stereogenic centres are generated by α-alkylation using the SAMP/RAMP hydrazone methodology and diastereoselective reduction of t
Enantioselective Alkylation of 2,2-Dimethyl-1,3-dioxan-5-one Using the SAMP-/RAMP-Hydrazone Method
Enders, Dieter,Bockstiegel, Bernhard
, p. 493 - 496 (2007/10/02)
The lithiated SAMP-hydrazone (S)-3 is used as a chiral 1,3-dihydroxyacetone-enolate equivalent C in overall enantioselective α-alkylations leading to 4-alkyl-2,2-dimethyl-1,3-dioxan-5-ones (S)-5a-i in good overall chemical yields and of high enantiomeric purity (ee = 88 - >/= 93percent.