4S,5S-[Bis(carbethoxy)]-2-ethenyl-1,3,2-dioxaborolane: A novel enantioselective dienophile

Tetrahedron Asymmetry

Volumn 8, Issue 8, 1997, Pages 1149-1152

  Bonk, Jason D ^a   Avery, Mitchell A ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANOL DERIVATIVE; ORGANOBORON DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030895029     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00122-5     Document Type: Article

References (19)

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10. Noiret, N.; Youssofi, A.; Carboni, B.; Vaultier, M. J. Chem. Soc. Chem. Commun. 1992, 1105-07.
11. Singleton, D. A.; Martinez, J. P.; Watson, J. V.; Ndip, G. M. Tetrahedron 1992, 48, 5831-5838.
12. Singleton, D. A.; Lee, Y.-K. Tetrahedron Lett. 1995, 36, 3473-3476.
13. Shimada, S.; Osoda, K.; Narasaka, K. Bull. Chem. Soc. Jpn 1993, 66, 1254-1257.
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18. Sybyl v.6.0, Tripos Associates, St. Louis.
19. 2, +1.033. Pertinent LUMO atomic coefficients for (+)-1: C1, -0.68; C2, +0.47; B, +0.47; C1 and C2 are the terminal and internal alkenyl carbons, respectively. Calculated with MOPAC v. 6.00 within Sybyl 6.0, Ref. 18. For a relevant discussion of FMO effects and comparative data, see Singleton, D. A.; Martinez, J. P. J. Am. Chem. Soc. 1990, 7423.