109333-88-2Relevant academic research and scientific papers
Anomalous threo-Diastereoselectivity in Allylic Silane- or Stannane-Aldehyde Condensation Reactions: New Interpretation of the Antiperiplanar vs. Synclinal Problem on the Transition-state Conformations
Mikami, Koichi,Kawamoto, Kazuya,Loh, Teck-Peng,Nakai, Takeshi
, p. 1161 - 1163 (1990)
Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or -stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.
Allylcopper intermediates with N-heterocyclic carbene ligands: Synthesis, structure, and catalysis
Russo, Vlncenzo,Herron, Jessica R.,Ball, Zachary T.
supporting information; experimental part, p. 220 - 223 (2010/03/30)
(Figure presented) Allylcopper Intermediates with N-heterocyclic carbene liganda are synthesized by transmetalation of allylsiloxane reagents, and the crystal structures of allylcopper compounds are reported. The allylcopper transmetalation is utilized fo
Total synthesis of GEX1A
Murray, Timothy J.,Forsyth, Craig J.
supporting information; experimental part, p. 3429 - 3431 (2009/05/11)
(Chemical Equation Presented) An efficient and readily modifiable synthesis of GEX1A/herboxidiene/TAN-1609 (1) was developed. This modular synthesis featured a Suzuki coupling to install the conjugated diene and a Ru-catalyzed lactonization and Roush crotylation to construct the functionalized tetrahydropyran moiety. Myers' alkylation, cross-metathesis, and Keck crotylation were employed for assembly of the biologically essential side-chain domain.
Chiral Synthesis via Organoboranes. 21. Allyl- and Crotylboration of α-Chiral Aldehydes with Diisopinocampheylboron as the Chiral Auxiliary
Brown, Herbert C.,Bhat, Krishna S.,Randad, Ramnarayan S.
, p. 1570 - 1576 (2007/10/02)
B-Allyldiisopinocampheylboranes have been screened for diastereofacial selectivity in their reaction with α-substituted chiral aldehydes.Both syn and anti products have been obtained in very high diastereoselectivities.Further, (E)-crotyldiisopinocampheylboranes and (Z)-crotyldiisopinocampheylboranes have been used for diastereofacial selectivity in their reaction with α-substituted chiral aldehydes.These crotylboranes, 20-23, are highly diastereoselective reagents and the corresponding (3,4- and 4,5-)-anti,syn, -anti,anti, and -syn,anti products have been obtained in very high facial selectivities; even the syn,syn product has been obtained in moderately good facial selectivity.Finally, the relative efficiences of the various chiral auxiliaries utilized in the literature for the allyl- and crotylboration have been compared with those achieved by the diisopinocampheylboron moiety.
