159854-34-9Relevant academic research and scientific papers
Asymmetric addition of allylic stannanes to aldehydes catalyzed by binap·Ag(I) complex
Yanagisawa,Nakashima,Nakatsuka,Ishiba,Yamamoto
, p. 1129 - 1137 (2007/10/03)
Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP·AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in TI-IF at
Indium-mediated γ-pentadienylation of aldehydes and ketones: Cross-conjugated trienes for diene-transmissive cycloadditions
Woo, Simon,Squires, Neil,Fallis, Alex G.
, p. 573 - 575 (2008/02/11)
(Matrix presented) Treatment of 5-bromo-1,3-pentadiene with indium metal in the presence of carbonyl compounds results in γ-pentadienylation to generate the 1,4-diene. Elimination of the resulting alcohol affords cross-conjugated triene systems which rapi
Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates
Kobayashi, Shu,Nishio, Koichi
, p. 6620 - 6628 (2007/10/02)
Allyltrichlorosilanes regioselectively reacted with aldehydes in N,N-dimethylformamide (DMF) without a catalyst to afford the corresponding homoallylic alcohols in high yields.The reactions proceeded under neutral conditions, and syn- and anti-homoallylic alcohols were stereoselectively obtained from (Z)- and (E)-allyltrichlorosilanes, respectively.In these reactions, DMF coordinated to the silicon atom of the allyltrichlorosilanes to form hypervalent silicates, which in turn reacted with aldehydes smoothly.Solvent effects in these reactions were also examined.The reactions were applied to the one-pot synthesis of homoallylic alcohols from allylic chlorides via organosilicon intermediates.While syn-homoallylic alcohols were prepared from (Z)-allyl chlorides, anti-homoallylic alcohols were obtained from (E)-allyl chlorides.Unique regioselectivities in the reactions of 1-chloro-2,4-pentadiene were also found.Finally, the one-pot synthesis of homoallylic alcohols from 1,3-dienes is reported.
