메뉴 건너뛰기




Volumn 19, Issue 24, 2008, Pages 2767-2770

Reversal of diastereoselectivity in the benzylation of the lithium enolates of phosphonopropanoamides by changing the base equivalents

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BASE; BENZYL BROMIDE; ENOLASE; LITHIUM; PHOSPHONOPROPANOAMIDE; POTASSIUM; SODIUM; UNCLASSIFIED DRUG;

EID: 59349119068     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.11.028     Document Type: Article
Times cited : (11)

References (64)
  • 3
    • 17744381382 scopus 로고    scopus 로고
    • For selected examples, see:
    • For selected examples, see:. Du D.M., Lu S.F., Fang T., and Xu J. J. Org. Chem. 70 (2005) 3712-3715
    • (2005) J. Org. Chem. , vol.70 , pp. 3712-3715
    • Du, D.M.1    Lu, S.F.2    Fang, T.3    Xu, J.4
  • 32
    • 0028880837 scopus 로고
    • For the synthesis of both enantiomers from a single chiral source via alkylations in the presence of additives, see:
    • For the synthesis of both enantiomers from a single chiral source via alkylations in the presence of additives, see:. Alvarez-Ibarra C., Csákÿ A.G., Maroto R., and Quiroga M.L. J. Org. Chem. 60 (1995) 7934-7940
    • (1995) J. Org. Chem. , vol.60 , pp. 7934-7940
    • Alvarez-Ibarra, C.1    Csákÿ, A.G.2    Maroto, R.3    Quiroga, M.L.4
  • 34
    • 0030010210 scopus 로고    scopus 로고
    • Stereochemical reversal has also been observed in the alkylation of enolates derived from (S,S)-pseudoephedrine on changing the alkylating agents:
    • Stereochemical reversal has also been observed in the alkylation of enolates derived from (S,S)-pseudoephedrine on changing the alkylating agents:. Meyers A.G., and McKinstry L. J. Org. Chem. 61 (1996) 2428-2440
    • (1996) J. Org. Chem. , vol.61 , pp. 2428-2440
    • Meyers, A.G.1    McKinstry, L.2
  • 35
    • 0034670608 scopus 로고    scopus 로고
    • For reviews on this subject, see:
    • For reviews on this subject, see:. Groaning M.D., and Meyers A.I. Tetrahedron 56 (2000) 9843-9872
    • (2000) Tetrahedron , vol.56 , pp. 9843-9872
    • Groaning, M.D.1    Meyers, A.I.2
  • 38
    • 0842328431 scopus 로고    scopus 로고
    • For the origin of stereochemical reversal in the alkylation of Meyers-type lactam enolate, see:
    • For the origin of stereochemical reversal in the alkylation of Meyers-type lactam enolate, see:. Ikuta Y., and Tomoda S. Org. Lett. 6 (2004) 189-192
    • (2004) Org. Lett. , vol.6 , pp. 189-192
    • Ikuta, Y.1    Tomoda, S.2
  • 45
    • 59349100958 scopus 로고    scopus 로고
    • note
    • 31P NMR at 81 MHz.
  • 47
    • 59349112389 scopus 로고    scopus 로고
    • note
    • When the benzylation of 1a was carried out using LDA (<2.0 equiv) the reaction was not complete.
  • 48
    • 59349121584 scopus 로고    scopus 로고
    • Identical results were obtained when LDA (3.0, 3.5 and 4.0 equiv) were used in the benzylation of 1a.
    • Identical results were obtained when LDA (3.0, 3.5 and 4.0 equiv) were used in the benzylation of 1a.
  • 52
    • 59349086727 scopus 로고    scopus 로고
    • note
    • Diethyl phosphonopropanoamides afforded a better E:Z selectivity than dimethyl phosphonopropanoamides in the HWE reaction, see: Ref. 14b.
  • 53
    • 0001681677 scopus 로고
    • For the influence of the base on the stereoselectivity of alkylation reactions, see:
    • For the influence of the base on the stereoselectivity of alkylation reactions, see:. Kawabata T., Wirth T., Yahiro K., Suzuki H., and Fuji K. J. Am. Chem. Soc. 116 (1994) 10809-10810
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10809-10810
    • Kawabata, T.1    Wirth, T.2    Yahiro, K.3    Suzuki, H.4    Fuji, K.5
  • 64
    • 59349121059 scopus 로고    scopus 로고
    • note
    • The silyl ether of enolate derived from 1a could not be isolated, even after several attempts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.