메뉴 건너뛰기




Volumn 49, Issue 25, 2010, Pages 4264-4268

Asymmetrie synthesis of allylsilanes by the borylation of lithiated carbamates: Formal total synthesis of (-)-decarestrictine D

Author keywords

Boranes; Borates; Homologation; Lithium natural products

Indexed keywords

ALLYLSILANES; BORATES; BORYLATION; CHEMICAL EQUATIONS; INVERSION OF CONFIGURATION; NATURAL PRODUCTS; TOTAL SYNTHESIS;

EID: 77953516846     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001223     Document Type: Article
Times cited : (76)

References (53)
  • 8
    • 0025601763 scopus 로고
    • Fleming-Tamao-oxidation
    • Some other selected applications are epoxidation/elimination: a) W. R. Roush, P. T. Grover, Tetrahedron Lett. 1990,31,7567-7570; Fleming-Tamao- oxidation:
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7567-7570
    • Roush, W.R.1    Grover, P.T.2
  • 16
    • 35048834773 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7491-7494.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7491-7494
  • 23
    • 77953513019 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 45, 6317-6319.
    • (2009) Angew. Chem. Int. Ed. , vol.45 , pp. 6317-6319
  • 26
    • 33947380529 scopus 로고    scopus 로고
    • For related double aliylboration reagents based on boron and silicon: a) F. Peng, D. G. Hall, J. Am. Chem. Soc. 2007, 129, 3070-3071;
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 3070-3071
    • Peng, F.1    Hall, D.G.2
  • 29
    • 35048817308 scopus 로고    scopus 로고
    • Reactions of sulfur ylides with, alkenyl 9-BBN derivatives and subsequent trapping with, aldehydes: a) G. Y. Fang, V. K. Aggarwal, Angew. Chem. 2007, 119, 363-366;
    • (2007) Angew. Chem , vol.119 , pp. 363-366
    • Fang, G.Y.1    Aggarwal, V.K.2
  • 30
    • 33846436053 scopus 로고    scopus 로고
    • Reactions of lithiated carbamates with unfunctionalized alkenyl 9-BBN derivatives and alkenyl boronic esters
    • Angew. Chem. Int. Ed. 2007, 46, 359-362; Reactions of lithiated carbamates with unfunctionalized alkenyl 9-BBN derivatives and alkenyl boronic esters:
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 359-362
  • 33
    • 0343177680 scopus 로고
    • The e.r. of stannane 12 is 95:5 (Chiral HPLC). Details of the optimization of the e.r. of the stannane (nature of Sn and N substituents) are given in the Supporting Information
    • Angew. Chem. Int. Ed. Engl. 1990, 29, 1424 -1425. The e.r. of stannane 12 is 95:5 (Chiral HPLC). Details of the optimization of the e.r. of the stannane (nature of Sn and N substituents) are given in the Supporting Information.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 1424-1425
  • 35
    • 0037048610 scopus 로고    scopus 로고
    • (+)-sparteine-surrogate behaves in an enantiocomplementary fashion to (-)-sparteine
    • M. J. Dearden, C. R. Firkin, J.-P. R. Hermet, P. O'Brien, J. Am. Chem. Soc. 2002, 124, 11870-11871; (+)-sparteine-surrogate behaves in an enantiocomplementary fashion to (-)-sparteine.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11870-11871
    • Dearden, M.J.1    Firkin, C.R.2    Hermet, J.-P.R.3    O'Brien, P.4
  • 37
    • 0029891973 scopus 로고    scopus 로고
    • There are a few examples where (-)-sparteine can be used to generate either enantiomer of a product, for example : Y. S. Park, M. L. Boys, P. Beak, J. Am. Chem. Soc. 1996, 118, 3757-3758.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3757-3758
    • Park, Y.S.1    Boys, M.L.2    Beak, P.3
  • 38
    • 77953532812 scopus 로고    scopus 로고
    • 3CCH= CH-B-9BBN) show intermediate reactivity with the same carbamates: 2b reacts with complete retention of configuration but 2 a reacts to give a mixture of products derived from retention and inversion of configuration, Carbamate 12 (diamine-free) reacts with complete retention of configuration; see: Ref. [12b]
    • 3CCH= CH-B-9BBN) show intermediate reactivity with the same carbamates: 2b reacts with complete retention of configuration but 2 a reacts to give a mixture of products derived from retention and inversion of configuration, Carbamate 12 (diamine-free) reacts with complete retention of configuration; see: Ref. [12b];
  • 40
    • 0026754759 scopus 로고
    • The triisopropoxytitanation of 1-oxy-2-alkenyllithium compounds proceeds with retention of configuration with the TMEDA complexes whereas the sparteine complexes react with inversion: c) O. Zschage, J.-R. Schwark, T. Krämer, D. Hoppe, Tetrahedron 1992, 48, 8377-8388.
    • (1992) Tetrahedron , vol.48 , pp. 8377-8388
    • Zschage, O.1    Schwark, J.-R.2    Krämer, T.3    Hoppe, D.4
  • 44
    • 77953490852 scopus 로고    scopus 로고
    • In comparison to reactions with boranes, reactions of lithiated carbamates with boronic esters have a greater tendency to occur with retention of configuration. This is probably because the lithium can complex with the oxygen atom of the boronic ester so that the boronic ester is delivered from, the same face as the metal ; see Ref. [8]
    • In comparison to reactions with boranes, reactions of lithiated carbamates with boronic esters have a greater tendency to occur with retention of configuration. This is probably because the lithium can complex with the oxygen atom of the boronic ester so that the boronic ester is delivered from, the same face as the metal ; see Ref. [8].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.